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[ CAS No. 72155-45-4 ] {[proInfo.proName]}

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Chemical Structure| 72155-45-4
Chemical Structure| 72155-45-4
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Product Details of [ 72155-45-4 ]

CAS No. :72155-45-4 MDL No. :MFCD00143854
Formula : C14H19NO3 Boiling Point : -
Linear Structure Formula :C4H9COOHNCH(CH2C6H5)CHO InChI Key :ZJTYRNPLVNMVPQ-LBPRGKRZSA-N
M.W : 249.31 Pubchem ID :6998013
Synonyms :

Safety of [ 72155-45-4 ]

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 [ 72155-45-4 ]

* 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 [ 72155-45-4 ]

[ 72155-45-4 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 6414-69-3 ]
  • [ 72155-45-4 ]
  • [ 207222-78-4 ]
  • 2
  • [ 72155-45-4 ]
  • [ 135383-60-7 ]
  • 3
  • [ 546-68-9 ]
  • [ 6414-69-3 ]
  • [ 72155-45-4 ]
  • [ 133333-27-4 ]
YieldReaction ConditionsOperation in experiment
5.95 g (88%) With acetic acid;titanium chloride; In dichloromethane; tert-butyl methyl ether; ISOPROPYLAMIDE; water; toluene; EXAMPLE 4 4A, (5S,1'S)-5-(1-(Boc-amino)-2-phenylethyl)dihydrofuran-2(3H)-one A mixture of 10.6 g (46.6 mmol) of <strong>[6414-69-3]<strong>[6414-69-3]ethyl 3-iodopropionat</strong>e</strong>, 4.9 g (75.3 mmol) of freshly prepared zinc-copper couple, 7.9 ml of dimethylacetamide and 79 ml of dry toluene was stirred under N2 atmosphere at ambient temperature for 1 h and at 80 C. for 4 h. The mixture was cooled to 20 C. and the excess zinc-copper couple allowed to settle. To a dry flask was added 10 ml of dry toluene, 56 ml of dry dichloromethane and 3.4 ml (11.4 mmol) of titanium isopropoxide. The solution was cooled to 15 C. and 3.6 ml (32.8 mmol) of titanium chloride was added dropwise (<25 C.). The solution was stirred at ambient temperature for 15 min, and then cooled to -40 C. The iodozinc-homoenolate supernatant was added by cannula to it (<25 C.). The resulting dark-red solution was stirred at -25 C. for 5 min and then cooled to -40 C. A solution of 5.5 g (22.1 mmol) of Boc-L-phenylalaninal in 20 ml of dichloromethane was added by cannula to it (<-40 C.). The reaction mixture was stirred vigorously at -20 C. for 24 h. The reaction was quenched by addition to a stirred mixture of 250 ml of water and 350 ml of tert-butyl methyl ether at 0 C. The aqueous phase was extracted with 250 ml of tert-butyl methyl ether. The combined organic phases were washed with water, saturated aqueous NaHCO3, water and brine, dried over MgSO4 and concentrated in vacuo to give crude hydroxyester as a white solid. The hydroxyester was dissolved in 180 ml of toluene and 5.5 ml of acetic acid and heated at reflux for 2.5 h. The mixture was cooled to ambient temperature, diluted with isopropyl acetate, washed with water, saturated aqueous NaHCO3, water and brine, dried over MgSO4 and concentrated in vacuo to give an oil which was crystallized from hexane to provide 5.95 g (88%) of desired compound as a white solid. 1 H NMR (CDCl3) delta1.37 (s, 9H), 2.14 (m, 2H), 2.52 (m, 2H), 2.84-3.00 (m, 2 H), 4.01 (m, 1H), 4.47 (td, 1H), 4.59 (br d, 1H), 7.24-7.32 (m, 5H). Mass spectrum: (M+H)+ =323.
  • 4
  • [ 2480-23-1 ]
  • [ 72155-45-4 ]
  • [ 1404073-22-8 ]
YieldReaction ConditionsOperation in experiment
93% With borane pyridine; acetic acid; In methanol; at 20℃; 100 mg (0.76 mmol) of commercially available <strong>[2480-23-1]N-methyl-L-valine</strong> and 285 mg (1.14 mmol) of commercially available tert-butyl (2S)-1-oxo-3-phenylpropan-2-yl carbamate were combined in 22 ml of methanol and admixed with 340 mg (3.66 mmol) of borane-pyridine complex and 70 μl of acetic acid. The reaction mixture was stirred at RT overnight. This was followed by concentration under reduced pressure, and the residue was purified by flash chromatography on silica gel with dichloromethane/methanol/17% aqueous ammonia solution as the eluent. After concentration of the corresponding fractions and lyophilization from 1:1 dioxane/ water, 259 mg (93% of theory) of the title compound were obtained. [2392] HPLC (Method 12): Rt=1.6 min; [2393] LC-MS (Method 11): Rt=0.76 min; MS (ESIpos): m/z=365 (M+H)+.
93% With borane-pyridine complex; acetic acid; In methanol; at 20℃; [4774] 100 mg (0.76 mmol) of commercially available<strong>[2480-23-1]N-methyl-L-valine</strong> and285 mg (1.14 mmol) of commerciallyavailable tert-butyl (2S)-1-oxo-3-phenylpropan-2-yl carbamatewere combined in 22 ml of methanol and admixed with340 mg (3.66 mmol) ofborane-pyridine complex and 70 fll ofacetic acid. The reaction mixture was stirred at RT overnight.This was followed by concentration in vacuo, and the residuewas purified by flash chromatography on silica gel withdichloromethane/methanol/17% aqueous ammonia solutionas the eluent. After concentration of the corresponding fractionsand lyophilization from 1:1 dioxane/water, 259 mg(93% of theory) of the title compound were obtained.[4775] HPLC (Method 12): R,=l.6 min;[4776] LC-MS (Method 11): R,=0.76 min; MS (ESipos):m/z=365 (M+Ht.
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