Water → 3-(Benzyloxycarbonyl-ethoxycarbonylmethyl-amino)-propionic acid ethyl ester

HRID 20918

Reaction equation

HRID 20918 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][NH:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:2].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].O>C(#N)C>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][N:7]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 10387Benzyl chloroformateHCID 281012Ethyl 3-(ethoxycarbonylmethylamino)propionate

Product 1

HCID 547587953-(Benzyloxycarbonyl-ethoxycarbonylmethyl-amino)-propionic acid ethyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of diester 58 (3.88 g, 20.2 mmol) in dry acetonitrile (40 mL) at 0° C., under Argon, was added slowly benzyl chloroformate (3.17 mL, 1.1 equiv.). The solution was stirred at 0° C. for 1 h after which it was poured into water (50 mL). The phases were separated and the aqueous layer was extracted with dichloromethane (3×50 mL). the combined organic extracts were washed with 5% HCl, water, brine and dried over anhydrous sodium sulfate. Evaporation of the solvents was followed by distillation to afford compound 70 as a colorless oil (5.4 g, 80%).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with dichloromethane (3×50 mL)
  3. washthe combined organic extracts were washed with 5% HCl, water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation of the solvents
  6. distillationwas followed by distillation

Sources & evidence

ORD record
ord-a1570b3dd2e94107a9b83918b3801240
Source dataset
uspto-grants-2010_06
Patent number
US07745608B2

Linked notes

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