Acetyl chloride → (S)-(+)-2-Phenylglycine methyl ester hydrochloride

HRID 322050

Reaction equation

HRID 322050 reaction equation
[C:1]([Cl:4])(=O)C.[CH:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH2:15])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1>CO>[CH3:1][O:13][C:12]([C@@H:11]([NH2:15])[C:8]1[CH:7]=[CH:6][CH:5]=[CH:10][CH:9]=1)=[O:14].[ClH:4]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 70134Phenylglycine, D-

Product 1

HCID 11217910(S)-(+)-2-Phenylglycine methyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetyl chloride (4 ml) was added cautiously and dropwise to methanol (20 ml) at 0° C. over 2 minutes. When the addition was completed, D-phenylglycine (1 g, 5.9 mmol, Aldrich) was introduced in a single portion. The mixture was stirred until dissolved then allowed to stand at RT for 24 hours. The solvent was evaporated then coevaporated twice from toluene to afford the title compound as a white crystalline solid in quantitative yield. The title compound was obtained as a white crystalline solid in quantitative yield with an identical n.m.r. spectrum to the L-isomer.

Workup

  1. additionWhen the addition
  2. dissolutionuntil dissolved
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-92368913d9c2407190b644d8376d9a3c
Source dataset
uspto-grants-2001_04
Patent number
US06211212B1

Linked notes

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