Chloroacetyl chloride → tert-butyl (2S)-2-(2-chloroacetamido)-3-phenylpropanoate

HRID 77515Notes

Reaction equation

HRID 77515 reaction equation
Cl.[C:2]([O:6][C:7](=[O:17])[C@@H:8]([NH2:16])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.[Cl:25][CH2:26][C:27](Cl)=[O:28]>ClCCl.O>[C:2]([O:6][C:7](=[O:17])[C@@H:8]([NH:16][C:27](=[O:28])[CH2:26][Cl:25])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 11459563L-Phenylalanine, 1,1-dimethylethyl ester, hydrochloride (1:1)

Product 1

HCID 86713545tert-butyl (2S)-2-(2-chloroacetamido)-3-phenylpropanoateYield 98.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3.0 g (11.6 mmol) (S)-2-amino-3-phenyl-propionic acid tert-butyl ester hydrochloride (Aldrich) and 3.32 mL (23.9 mmol) triethylamine (Aldrich) in dichloromethane (30 mL), 0.97 mL (12.2 mmol) chloroacetyl chloride (Aldrich) is added dropwise and the resulting mixture is stirred at room temperature for 4 h. The reaction mixture is diluted with water (25 mL), the organic layer is separated, washed with 10% NaHCO3 solution (25 mL), dried (MgSO4) and finally evaporated under reduced pressure to yield the title compound (3.4 g).

Workup

  1. additionis added dropwise
  2. customthe organic layer is separated
  3. washwashed with 10% NaHCO3 solution (25 mL)
  4. dry with materialdried (MgSO4)
  5. customfinally evaporated under reduced pressure

Sources & evidence

ORD record
ord-45ac19933d4f45b99cbb5458dd73736d
Source dataset
uspto-grants-2014_09
Patent number
US08841309B2

Reaction notes

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