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[ CAS No. 162537-11-3 ] {[proInfo.proName]}

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Chemical Structure| 162537-11-3
Chemical Structure| 162537-11-3
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Product Details of [ 162537-11-3 ]

CAS No. :162537-11-3 MDL No. :MFCD07778455
Formula : C8H15NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :NWPRXAIYBULIEI-RXMQYKEDSA-N
M.W : 189.21 Pubchem ID :11263950
Synonyms :
Chemical Name :(S)-2-((Methoxycarbonyl)amino)-3,3-dimethylbutanoic acid

Calculated chemistry of [ 162537-11-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 46.56
TPSA : 75.63 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.51
Log Po/w (XLOGP3) : 1.3
Log Po/w (WLOGP) : 0.84
Log Po/w (MLOGP) : 0.51
Log Po/w (SILICOS-IT) : -0.17
Consensus Log Po/w : 0.8

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.5
Solubility : 5.95 mg/ml ; 0.0315 mol/l
Class : Very soluble
Log S (Ali) : -2.49
Solubility : 0.614 mg/ml ; 0.00325 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.64
Solubility : 43.0 mg/ml ; 0.228 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.36

Safety of [ 162537-11-3 ]

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 [ 162537-11-3 ]

* 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 [ 162537-11-3 ]

[ 162537-11-3 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 162537-11-3 ]
  • 1-[4-(pyridin-2-yl)phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane trihydrochloride [ No CAS ]
  • [ 198904-31-3 ]
YieldReaction ConditionsOperation in experiment
84% With 4-methyl-morpholine; diisopropyl-carbodiimide; In dichloromethane; isopropyl alcohol; at -10 - 20℃;Inert atmosphere;Product distribution / selectivity; Example 1 : Preparation of atazanavir using 1 equivalent of compound (II), 3.5 equivalents of compound (III), 3.5 equivalents of DIC, and 6.6 equivalents of NMM97.5 g of 1 -[4-(piridyn-2-yl)phenyl-4(S)-hydroxy]-5-(S)-2,5-diamino-6-phenyl- 2-azahexane trihydrochloride (trihydrochloride of compound (II) with a 10%wt content of isopropanol, 185.97mmol) were suspended into 683 ml of dichloromethane under nitrogen atmosphere at -10 0C. 135 ml_ (1227.40 mmol) of /V-methylmorpholine were added maintaining the temperature at -10 0C.Separately, 100.8 ml_ (650.90 mmol) of N,N-diisopropylcarbodiimide were added to a suspension of 123.2 g (650.90 mmol) of N-(methoxycarbonyl)-L- tert-leucine (compound (III)) into 975 ml of dichloromethane.Then, the first suspension was quickly transferred over the second one. The resulting mixture was warmed up to room temperature and was maintained at such temperature until the reaction was completed (93% atazanavir by HPLC, monoimpurity content: 1.2%). The reaction mixture was filtered off and was washed with 800 ml_ of water. Then, the organic phase was concentrated up to half volume and 500 ml_ of tert-butylmethylether were added. The mixture was concentrated again up to half volume. This operation was repeated three times up to a dichloromethane content equal or less to 20%. The precipitated product was recovered by filtration. 125.4 g of atazanavir were obtained (Yield =96%). Purity by High Performance Liquid Chromatography (HPLC) = 98.2%, with 4% of N,N-diisopropylurea (DIU) and free of the other probable diastereomers. Molar yield =92%. Recrystallization in ethanol/water 45:55 yielded 105.34 g of atazanavir (149.5 mmol). Recrystallization yield: 84%. Purity HPLC = 99.4%, free of DIU, and free of the other probable diastereomers.The formula of the three probable diastereomers and the HPLC conditions to detect their presence are included below:d-ld-ll d-lHPLC conditions:Liquid chromatograph with UV detector equipped with automatic injector, and integration systemColumn: ZORBAX Eclipse XDB-C18 150x4.6 mm, 5mum.Mobile phase: A (0.05% formic acid in water) and B (ACN)Gradient elution:Detection: 254 nmFlow: 1 mL/minColumn temperature: 25 0CInjection: 2 muLTime injection and chromatogram: 20 minRelative retention time of the diastereomers (RRT):
  • 2
  • [ 857900-54-0 ]
  • [ 162537-11-3 ]
  • [ 198904-31-3 ]
  • 3
  • [ 162537-11-3 ]
  • [ 198904-31-3 ]
  • 4
  • (2S,3S)-3-amino-4-phenyl-1-(1-(4-(pyridin-2-yl)benzyl)hydrazinyl)butan-2-ol hydrochloride [ No CAS ]
  • [ 162537-11-3 ]
  • [ 198904-31-3 ]
YieldReaction ConditionsOperation in experiment
To another flask N-methoxycarbonyl-(L)-tertiary leucine (V) (88.1 1 g, 0.47 mole), 1- (3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (89.4 g, ' 0.47 mole), 1 -Hydroxy-benzotriazole (HOBT) (75.5 g, 0.49 mole) and dichloromethane (1000 mL) were charged and stirred at 25 - 30C for 4 - 5 hours. The aqueous layer of diamino compound (IV) obtained above in part A, and N, N-diisopropylethyl amine (DIPEA) (182.8 mL, 138 g) were added and stirred for 3 hours. The reaction mass was then washed with water, sodium bicarbonate solution and brine. The dichloromethane layer was concentrated to 100 - 150 ml_. Ethyl acetate (1000 ml.) was added and about half of the mixture of solvent was distilled out. n-Heptane (400 mL) was added and stirred for 1 hour at 65C. Cooled to 30C, solid was filtered, washed with mixture of ethyl acetate and n-heptane and dried to afford 101' g of atazanavir base (crude).
  • 5
  • [ 162537-11-3 ]
  • 1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane dihydrochioride [ No CAS ]
  • [ 198904-31-3 ]
YieldReaction ConditionsOperation in experiment
Example 6: Preparation of Atazanavir Formula IX To N-methoxycarbonyl-(L)-tert-leucine (65.72 g), 1 -hydroxybenzotriazole (HOBT; 51.19 g) was added at ambient temperature under nitrogen atmosphere and the reaction mixture was cooled to 0C to -5C. Triethylamine (79.81 g) was slowly added to the reaction mixture at 0C to -5C and further dichloromethane (1600 mL) was added at ambient temperature. Thionyl chloride (43.20 g) was slowly added over a period of 1 hour to 1.5 hours at 0C to -5C under nitrogen atmosphere and the reaction mixture was stirred at 10C to 15C for 1.5 hours to 2 hours. De-ionized water (1000 mL) was added and the reaction mixture was stirred for 10 minutes to 15 minutes at 10C to 15C. The organic layer was separated and dipotassium hydrogen orthophosphate (K2HPO4; 480g/2000 mL de-ionized water) was added at 10C to 15C. The aqueous layer of dihydrochloride salt of l-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)- tert-leucyl)amino-6-phenyl-2-azahexane (as obtained in Example 5) was added to the organic layer over a period of 1.5 hours to 2 hours at 10C to 15C. This reaction mixture was stirred for 12 hours to 14 hours at 30C to 35C. The completion of the reaction was monitored by HPLC. After completion of the reaction, the reaction mixture was cooled to 20C to 25C and the organic layer was separated. The organic layer was sequentially washed with an aqueous solution of potassium hydrogen sulfate (20 g/1000 mL de-ionized water), an aqueous solution of potassium carbonate (120 g/1000 mL de-ionized water) and de-ionized water (1000 mL). The organic layer so obtained was heated to 40C to 45C to recover dichloromethane atmospherically and then vacuum was applied for 50 minutes to 60 minutes at the same temperature. Methanol (1400 mL) was added to the mass so obtained at 40C to 45C and the reaction mixture was further heated to 60C to 68C. De-ionized water (1200 mL) was slowly added over a period of 30 minutes to 45 minutes at 60C to 68C. The reaction mixture was heated to reflux at 72C to 78C for 30 minutes. The reaction mixture was cooled to 20C to 25C and stirred for 2 hours to 3 hours. The solid was filtered and the wet cake was washed with a mixture of methanol (200 mL) and de-ionized water (200 mL). The solid so obtained was washed with toluene (1000 mL) and dried at 60C to 65C to afford the title compound. Yield(w/w): 1.0
Example 6 Preparation of Atazanavir To N-methoxycarbonyl-(L)-tert-leucine (65.72 g), 1-hydroxybenzotriazole (HOBT; 51.19 g) was added at ambient temperature under nitrogen atmosphere and the reaction mixture was cooled to 0 C. to -5 C. Triethylamine (79.81 g) was slowly added to the reaction mixture at 0 C. to -5 C. and further dichloromethane (1600 mL) was added at ambient temperature. Thionyl chloride (43.20 g) was slowly added over a period of 1 hour to 1.5 hours at 0 C. to -5 C. under nitrogen atmosphere and the reaction mixture was stirred at 10 C. to 15 C. for 1.5 hours to 2 hours. De-ionized water (1000 mL) was added and the reaction mixture was stirred for 10 minutes to 15 minutes at 10 C. to 15 C. The organic layer was separated and dipotassium hydrogen orthophosphate (K2HPO4; 480 g/2000 mL de-ionized water) was added at 10 C. to 15 C. The aqueous layer of dihydrochloride salt of 1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-tert-leucyl)amino-6-phenyl-2-azahexane (as obtained in Example 5) was added to the organic layer over a period of 1.5 hours to 2 hours at 10 C. to 15 C. This reaction mixture was stirred for 12 hours to 14 hours at 30 C. to 35 C. The completion of the reaction was monitored by HPLC. After completion of the reaction, the reaction mixture was cooled to 20 C. to 25 C. and the organic layer was separated. The organic layer was sequentially washed with an aqueous solution of potassium hydrogen sulfate (20 g/1000 mL de-ionized water), an aqueous solution of potassium carbonate (120 g/1000 mL de-ionized water) and de-ionized water (1000 mL). The organic layer so obtained was heated to 40 C. to 45 C. to recover dichloromethane atmospherically and then vacuum was applied for 50 minutes to 60 minutes at the same temperature. Methanol (1400 mL) was added to the mass so obtained at 40 C. to 45 C. and the reaction mixture was further heated to 60 C. to 68 C. De-ionized water (1200 mL) was slowly added over a period of 30 minutes to 45 minutes at 60 C. to 68 C. The reaction mixture was heated to reflux at 72 C. to 78 C. for 30 minutes. The reaction mixture was cooled to 20 C. to 25 C. and stirred for 2 hours to 3 hours. The solid was filtered and the wet cake was washed with a mixture of methanol (200 mL) and de-ionized water (200 mL). The solid so obtained was washed with toluene (1000 mL) and dried at 60 C. to 65 C. to afford the title compound.
  • 6
  • [ 162537-11-3 ]
  • 1-[4-(pyridin-2-yl)phenyl]-2,5-bis[N-(methoxycarbonyl)-L-tert-leucinyl]amino}-4(S)-hydroxy-6-phenyl-2-azahexane [ No CAS ]
  • [ 198904-31-3 ]
  • 7
  • 1-[4-(pyridine-2-yl)-phenyl]-4(S)-hydroxy-(5S)-2,5-diamino-6-phenyl-2-azahexane [ No CAS ]
  • [ 162537-11-3 ]
  • [ 198904-31-3 ]
YieldReaction ConditionsOperation in experiment
91.6% With pyridine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; at 35℃; for 1.5h; At 35 & lt; 0 & gt; C,A solution of 1- [4- (pyridin-2-yl) -phenyl] -4 (S) -hydroxy-5 (S) -2,5-diamino-6-phenyl-2-azacyclohexane (100 mmol), N-methoxycarbonyl-L-tert-leucine (37.8 g, 200.0 mmol)76.0 g (200 mmol) of HATU and 71.2 g of pyridine were placed in a 500 mL eggplant vial,Add 200mL methyl isobutyl ketone stirring 1h, TLC detection, reaction completed,The reaction solution was washed with 10% potassium dihydrogen phosphate and purified water in an order of 200 mL x 2, and the aqueous layer was discarded,The organic phase was dried over anhydrous sodium sulfate for 6 h and then filtered, and the filtrate was heated to 50 C,While adding 0.4g of charcoal charcoal 767 for decolorization, stirring 20min, cold to 20-30 filter,The organic phase was concentrated in vacuo,To the above oil was added 300 mL of ethanol and heated to reflux at 80 C to dissolve it all,And then 300mL of petroleum ether added to the hot solution, after the end of the natural cooling to 20-30 , and stirring 24h,The filter cake was washed twice with 30 mL of a mixed solvent of ethanol / petroleum ether = 1: 1, dried at 55 C for 12 h,64.5 g of finished azazanavir monomer, yield 91.6%, purity 99.9%.
  • 8
  • [ 162537-11-3 ]
  • [ 437713-06-9 ]
  • [ 198904-31-3 ]
YieldReaction ConditionsOperation in experiment
74.2% To 100 mL of N-methoxycarbonyl-L-tert-leucine was placed in a 500 mL Erlenmeyer flask, 200 mL of methylene chloride was added and stirred to dissolve, and then triethylamine 70.5 g and 14.2 g (112. Ommol) of thionyl chloride were added and the temperature was raised to 42 C. The solvent was diluted with methylene chloride. The mixture was allowed to cool for 3 h. The reaction was completed and the temperature was reduced to room temperature. The triethylamine hydrochloride solid was removed by filtration.use.The solid product (32.58 g, 90 mmol) in Example 1 was dissolved in 50 mL of dichloromethane, and the filtrate was slowly added dropwise to the system at room temperature. The mixture was stirred overnight and the reaction was completed.The reaction solution was washed successively with 10% citric acid, 10% potassium carbonate, 10% sodium chloride and purified water to 300 mL of X, concentrated under reduced pressure to about dichloromethane content of less than about 20%, and 191.43 mL of methyl tert Butyl ether, beating, filtration, vacuum 50 C to dry 54.3 g of the crude azazavir monomer, and the crude product was purified in a 1: 1 by volume ratio of ethanol: water to give anazanavir monomer 47. 1g, yield 74.2%.
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