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[ CAS No. 936-59-4 ] {[proInfo.proName]}

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Chemical Structure| 936-59-4
Chemical Structure| 936-59-4
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Product Citations

Product Citations

Canale, Vittorio ; Czekajewska, Joanna ; Klesiewicz, Karolina , et al. DOI: PubMed ID:

Abstract: The alarming increase in the resistance of bacteria to the currently available antibiotics necessitates the development of new effective antimicrobial agents that are active against bacterial pathogens causing major public health problems. For this purpose, our inhouse libraries were screened against a wide panel of clin. relevant Gram-pos. and Gram-neg. bacteria, based on which compound I was selected for further optimization. Synthetic efforts in a group of arylurea derivatives of aryloxy(1-phenylpropyl) alicyclic diamines, followed with an in vitro evaluation of the activity against multidrug-resistant strains identified compound 44 (1-(3-chlorophenyl)-3-(1-{3-phenyl-3-[3-(trifluoromethyl)phenoxy] propyl}piperidin-4-yl)urea). Compound 44 showed antibacterial activity against Gram-pos. bacteria including fatal drug-resistant strains i.e., Staphylococcus aureus (methicillin-resistant, MRSA; vancomycin-intermediate, VISA) and Enterococcus faecium (vancomycin-resistant, VREfm) at low concentrations (0.78-3.125 μg/mL) comparable to last resort antibiotics (i.e., vancomycin and linezolid). It is also potent against biofilm-forming S. aureus and Staphylococcus epidermidis (including linezolid-resistant, LRSE) strains, but with no activity against Gram-neg. bacteria (Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa). Compound 44 showed strong bactericidal properties against susceptible and drug-resistant Gram-pos. bacteria. Depolarization of the bacterial cytoplasmic membrane induced by compound 44 suggests a dissipation of the bacterial membrane potential as its mechanism of antibacterial action. The high antimicrobial activity of compound 44, along with its selectivity over mammalian cells (lung MCR-5 and skin BJ fibroblast cell lines) and no hemolytic properties toward horse erythrocytes, proposes arylurea derivatives of aryloxy(1-phenylpropyl) alicyclic diamines for development of novel antibacterial agents.

Keywords: Arylurea derivatives ; Antibacterial properties ; Anti-MRSA activity ; Anti-VRE activity ; Anti-LRSE activity ; Depolarization of bacterial cell membrane

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Product Details of [ 936-59-4 ]

CAS No. :936-59-4 MDL No. :MFCD00000990
Formula : C9H9ClO Boiling Point : -
Linear Structure Formula :- InChI Key :KTJRGPZVSKWRTJ-UHFFFAOYSA-N
M.W : 168.62 Pubchem ID :70295
Synonyms :
β-Chloroethyl phenyl ketone

Calculated chemistry of [ 936-59-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.24
TPSA : 17.07 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 2.24
Log Po/w (WLOGP) : 2.5
Log Po/w (MLOGP) : 2.4
Log Po/w (SILICOS-IT) : 3.0
Consensus Log Po/w : 2.41

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.5
Solubility : 0.53 mg/ml ; 0.00315 mol/l
Class : Soluble
Log S (Ali) : -2.23
Solubility : 0.984 mg/ml ; 0.00583 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.76
Solubility : 0.029 mg/ml ; 0.000172 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.07

Safety of [ 936-59-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 936-59-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 936-59-4 ]

[ 936-59-4 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 936-59-4 ]
  • [ 126712-07-0 ]
  • 3-(2-Bromo-6-methoxy-benzylamino)-1-phenyl-propan-1-ol [ No CAS ]
  • 2
  • [ 936-59-4 ]
  • [ 22693-41-0 ]
  • 1-Phenyl-3-[(2,4,6-triisopropylphenyl)sulfanyl]propan-1-one [ No CAS ]
  • 3
  • [ 936-59-4 ]
  • [ 21970-65-0 ]
YieldReaction ConditionsOperation in experiment
98% Present intermediate 3 was prepared in the same way as intermediate 14 of WO 2004/011436, i.e. according to Example A9 of WO 2004/011436, but starting from 3-chloropropiophenone. Yield: 98% of present intermediate 3
  • 4
  • [ 936-59-4 ]
  • [ 14814-17-6 ]
  • [ 128607-22-7 ]
YieldReaction ConditionsOperation in experiment
96% With titanium tetrachloride; zinc; In 2-methyltetrahydrofuran; at 15 - 50℃;Product distribution / selectivity; Hydroxyethoxybenzophenone (67.66g, 279.3 mmol, 1 eq), 3- chloropropiophenone (47.24 g, 279.3 mmol, 1 eq), zinc powder (69.45 g, 1062 mmol, 3.8 eq) and 2-methyltetrahydrofuran (895 g, 1041 ml) were charged to the reactor. The slurry was degassed and the vessel was filled with nitrogen gas. The slurry was cooled to <15C and then titanium tetrachloride (101.5 g, 535.1 mmol, 1.92 eq.) was slowly dosed maintaining a temperature below 20C. The slurry was heated to 50C and the temperature was maintained for 15 minutes. The slurry was heated to 70C and the pressure was reduced and 2- methyltetrahydrofuran (403 g) was distilled off at 70C and 650 mbar over 1 hour. Zinc(s) was filtered off and the filter was rinsed with 2-methyltetrahydrofuran (64 g). The pressure was reduced to 200 mbar and 2-methyltetrahydrofuran (344 g) was distilled off at 43-53C and 200-160 mbar pressure (total amount of pure 2- methyltetrahydrofuran recycled is 76%). Toluene (151g) was charged. A mixture of hydrochloric acid (aq) (116 g, 37 %) and water (281 g) was added maintaining a temperature below 20C. The lower aqueous phase was cut (at 30C) and discarded. Water (128 g) was added. The lower aqueous phase was cut (at 55C) and discarded. Water (131 g) was added again and the lower aqueous phase was cut again (at 55C) and discarded. The pressure was reduced and 2- methyltetrahydrofuran + toluene + water was distilled off at 150-50 bar and 37- 60C until there was a residual volume of about 130 ml. Before the crystallisation/precipitation process, the ratio of Z:E isomers of Ospemifene was about 5.5:1. Then, methanol (125 g) was charged and the solution was filtered. To the filtrate was added methanol to a total weight of 572 g (content estimated to 121 g raw product + toluene and 451 g methanol). Water (148 g) was added to the filtrate and the solution was heated to 50C. The solution was then cooled to 48C and seeded. The mixture was slowly cooled to 15C over 5 hours and maintained at this temperature overnight. The product was isolated by filtration and the filter cake was rinsed with methanol(aq) (74%, 141 g). Yield 50.4 g after drying (47.6%). Purity >99% by HPLC (standard). The raw product contained 98.81 % Z-isomer, 0.61% E-isomer (hence a Z:￡ ratio of 162:1 ) and 0.58% of other products. The product obtained (in a yield of 96%; hence, advantageously yield is not significantly decreased) after recrystallisation was 99.9% Z-isomer, 0.05% E-isomer (hence a Z:E ratio of 1991 : 1 ) and 0.05% of other products. Hence, an extremely pure and selective Z-isomer of the compound of formula I is obtained by this method of the invention.
With titanium tetrachloride; zinc; In 2-methyltetrahydrofuran; at -10 - 80℃; for 5.5h;Inert atmosphere; Zn powder (172 g, 2.6 mol) was added to the 3 L reaction flask, respectively2-methyltetrahydrofuran (1800 mL),Stir well and cool to -10 C,Nitrile was slowly added, TiCl4 (250 g, 1.32 mol) was slowly added dropwise,Add to warm up to room temperature for 30min,And then heated to 80 C for 2 h.Cooling to 40 ,A solution of 2- (4-benzophenoxy) -1-ethanol (108 g, 0.45 mol) was added dropwise3-chlorophenylacetone (76 g, 0.45 mol)2-methyltetrahydrofuran solution (800 ml).Plus heating temperature to 80 under the reaction 3h,After TLC detection reaction is completed,React and cool the system temperature to room temperature
  • 5
  • [ 936-59-4 ]
  • [ 613-87-6 ]
  • [ 100306-34-1 ]
  • [ 100306-33-0 ]
  • [ 93-55-0 ]
YieldReaction ConditionsOperation in experiment
With yeast strain Aureobasidium pullulans CQA; at 28℃; for 48h;Microbiological reaction; Enzymatic reaction; General procedure: Fresh plates of each yeast strain were streaked from the frozen stock in PDA. A single colony was used to inoculate 100mL of YM Broth. The culture was incubated at 28C and 150rpm for 48h and the cells were collected by centrifugation at 4000rpm and 4C for 15min. The pellet was washed three times with 50mL physiological serum. Afterward, 2g of yeast cells (wet weight) were suspended in 20mL of 10% dextrose solution and 30mg of the appropriate substrate were added. The culture was incubated at 28C and 150rpm in an orbital shaker ZHICHENG ZHWY-211B for 48h.
30%Chromat.; 23%Chromat. With yeast culture of Candida viswanathii KCh 120; In acetone; at 25℃; for 6h;Microbiological reaction; General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3-7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
  • 6
  • [ 936-59-4 ]
  • [ 613-87-6 ]
  • [ 93-55-0 ]
YieldReaction ConditionsOperation in experiment
With yeast strain Rhodotorula glutinis H93; at 28℃; for 48h;Microbiological reaction; Enzymatic reaction; General procedure: Fresh plates of each yeast strain were streaked from the frozen stock in PDA. A single colony was used to inoculate 100mL of YM Broth. The culture was incubated at 28C and 150rpm for 48h and the cells were collected by centrifugation at 4000rpm and 4C for 15min. The pellet was washed three times with 50mL physiological serum. Afterward, 2g of yeast cells (wet weight) were suspended in 20mL of 10% dextrose solution and 30mg of the appropriate substrate were added. The culture was incubated at 28C and 150rpm in an orbital shaker ZHICHENG ZHWY-211B for 48h.
91%Chromat.; 9%Chromat. With yeast culture of Rhodotorula rubra KCh 82; In acetone; at 25℃; for 24h;Microbiological reaction; General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3-7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
  • 7
  • [ 936-59-4 ]
  • [ 613-87-6 ]
YieldReaction ConditionsOperation in experiment
96% With formic acid; C30H31ClN2O2RuS; triethylamine; at 60℃; for 1.5h;Inert atmosphere; This compound is known [17]. From 3-chloropropiophenone 13: A degassed solution of 3-chloropropiophenone (170 mg, 1.01 mmol, 1.0 eq) and (S,S)-2 (3.1 mg, 0.005 mmol, 0.5%) in FA/TEA (5:2, 0.5 mL) was stirred at 60 C for 1.5 h. The mixture was diluted with ethyl acetate (5 mL) and quenched with NaHCO3 (sat., 5 mL), the aqueous layer was extracted further with ethyl acetate (2 5 mL) and the organic extracts dried over Na2SO4 and concentrated to give a brown oil. The crude was dissolved in diethyl ether and passed through a silica plug to yield the product 14 as a red oil (123 mg, 0.97 mmol, 96%) in 100% conv and 95% ee as measured by GC. [α]D22 -43.5 (c 0.35 in CHCl3); lit [17] [α]D22 -43.6 (S) (c 1.0 in CHCl3); δH (300 MHz, CDCl3) 7.29-7.15 (5H, m, Ph), 4.49 (1H, dt, J = 3.2, 6.6 Hz, CHOH), 1.85 (1H, brs, OH), 1.78-1.57 (2H, m, CH2), 0.82 (3H, t, J = 7.4 Hz, CH3); δC (75 MHz, CDCl3) 143.9, 127.8, 126.9, 125.4, 75.4, 31.3, 9.5; Chiral GC; (CP-Chirasil-Dex-Cβ, 25 m 0.25 mm x 0.25 μm column, oven: hold 12 min at 125 C, then ramp 1 C/min, final temp 145 C, inj.: split 220 C, det.: FID 250 C, 18 Psi He), retention times: 11.2 (R) and 11.4 (S) minutes. From phenyl vinyl ketone 15: Compound 14 could also be prepared with 100% conversion and 95% ee with the same method, starting from 15 (prepared by elimination of HCl from 3-chloropropriophenone [18], 126 mg, 0.95 mmol, 1 eq), (S,S)-2 catalyst (3.5 mg, 0.006 mmol, 0.5%) and FA/TEA (5:2, 0.5 mL). The product was isolated as a clear oil (103 mg, 0.76 mmol, 79%). Attempted reduction of 1-phenylprop-2-en-1-ol 17. Application of the same method to commercially available α-vinylbenzyl alcohol 17 (134 mg) and (S,S)-2 catalyst (3.3 mg, 5 μmol, 0.5%) in FA/TEA (5:2. 0.5 mL) gave no reaction in 1.5 h at 60 C.
100%Chromat. With yeast culture of Rhodotorula marina KCh 77; In acetone; at 25℃; for 144h;Microbiological reaction; General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3-7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
  • 8
  • [ 936-59-4 ]
  • [ 1565-74-8 ]
  • [ 613-87-6 ]
  • [ 100306-34-1 ]
  • [ 100306-33-0 ]
  • [ 93-55-0 ]
YieldReaction ConditionsOperation in experiment
21%Chromat. With yeast culture of Aphanocladium album KCh 417; In acetone; at 25℃; for 144h;Microbiological reaction; General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3-7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
33%Chromat. With yeast culture of Saccharomyces cerevisiae KCh 464; In acetone; at 25℃; for 144h;Microbiological reaction; General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3-7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
33%Chromat. With yeast culture of Saccharomyces pastorianus KCh 906; In acetone; at 25℃; for 24h;Microbiological reaction; General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3-7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
  • 9
  • [ 936-59-4 ]
  • [ 1565-74-8 ]
  • [ 613-87-6 ]
  • [ 100306-34-1 ]
  • [ 93-55-0 ]
YieldReaction ConditionsOperation in experiment
7%Chromat.; 21%Chromat. With yeast culture of Rhodotorula rubra KCh 4; In acetone; at 25℃; for 24h;Microbiological reaction; General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3-7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
  • 10
  • [ 936-59-4 ]
  • [ 1565-74-8 ]
  • [ 613-87-6 ]
  • [ 93-55-0 ]
YieldReaction ConditionsOperation in experiment
32%Chromat. With yeast culture of Rhodotorula rubra KCh 4; In acetone; at 25℃; for 216h;Microbiological reaction; General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3-7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
8%Chromat. With yeast culture of Yarrowia lipolytica 1-101-1,31-K1; In acetone; at 25℃; for 216h;Microbiological reaction; General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3-7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
58%Chromat. With yeast culture of Yarrowia lipolytica ATCC 32-338 A; In acetone; at 25℃; for 72h;Microbiological reaction; General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3-7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
  • 11
  • [ 936-59-4 ]
  • [ 613-87-6 ]
  • [ 18776-12-0 ]
  • [ 93-55-0 ]
YieldReaction ConditionsOperation in experiment
34%Chromat.; 6%Chromat.; 60%Chromat. With yeast culture of Rhodotorula rubra KCh 82; In acetone; at 25℃; for 6h;Microbiological reaction; General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3-7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
  • 12
  • [ 615-37-2 ]
  • [ 936-59-4 ]
  • [ 22966-01-4 ]
YieldReaction ConditionsOperation in experiment
87% With palladium diacetate; potassium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 20 - 90℃; under 750.075 Torr; for 16h;Inert atmosphere; General procedure: A mixture of Pd(OAc)2 (4.5 mg, 0.02 mmol), PPh3 (11.2 mg, 0.04 mmol), iodobenzene (1a) (82 mg, 0.4mmol), 3-chloropropiophenone (2a) (87 mg, 0.5 mmol), and K2CO3 (166 mg, 1.2 mmol) in DMF (2.5 mL) was stirred under a N2 atmosphere at room temperature for 10 min, and then heated at 90 C for 16 h. The reaction was then cooled to ambient temperature and diluted with CH2Cl2 (10 mL) before being filtered through a short pad of silica gel. The silica pad was rinsed with DCM (5 mL), and the combined filtrates were washed with brine (15 mL), dried over anhydrous Na2SO4. The solvent was then removed under reduced pressure to give the crude product as a residue, which was purified by silica gel column chromatography eluting with a mixture of petroleum ether (60-90 C)/EtOAc (v/v = 30:1).
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