Ammonia → Methyl (alphaS)-alpha-amino-2-chlorobenzeneacetate

HRID 1422296Notes

Reaction equation

HRID 1422296 reaction equation
Cl.[NH2:2][C@@H:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14])[C:4]([O:6][CH3:7])=[O:5].C(OCC)(=O)C.N.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[NH2:2][C@@H:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14])[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 24887640Benzeneacetic acid, alpha-amino-2-chloro-, methyl ester, hydrochloride (1:1), (alphaS)-

Product 1

HCID 11745652Methyl (alphaS)-alpha-amino-2-chlorobenzeneacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.36 g (10-2 mol) of methyl (+)-(S)-α-amino-α-(2-chlorophenyl)acetate hydrochloride are introduced into 50 ml of ethyl acetate or of methylene chloride, and 20 ml of 1.5 M aqueous ammonia or of sodium bicarbonate at 5% are added. The medium is stirred, the organic phase is separated after settling out and the aqueous phase is extracted with 10 ml of ethyl acetate. The organic phases are pooled, treated with anhydrous sodium sulphate and concentrated under reduced pressure until distillate is absent. The residue consisting of methyl (+)-(S)-α-amino-α-(2-chlorophenyl)acetate is then taken up in 50 ml of acetic acid.

Workup

  1. additionare added
  2. customthe organic phase is separated
  3. extractionthe aqueous phase is extracted with 10 ml of ethyl acetate
  4. additiontreated with anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure until distillate

Sources & evidence

ORD record
ord-52cbdf1be61241a4a712b4318971f073
Source dataset
uspto-grants-2000_06
Patent number
US06080875

Reaction notes

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