Methanol → methyl (2R)-2-amino-3-phenylpropanoate;hydrochloride

HRID 2302208

Reaction equation

HRID 2302208 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C@@H:6]([C:14]([OH:16])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[CH3:18]O>>[NH2:5][C@@H:6]([C:14]([O:16][CH3:18])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[ClH:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 13000988D-phenylalanine hydrochloride

Product 1

HCID 11481330methyl (2R)-2-amino-3-phenylpropanoate;hydrochloride

Procedure

To cold (−20° C.) and dry methanol (1 l) was added dropwise thionylchloride (130 ml). H—D-Phe-OH.HCl (147.6 g) was added and the reaction mixture was heated under reflux for 30 min and then kept at room temperature overnight. The mixture was concentrated in vacuo and coevaporated with methanol (3 times). The residue was crystallized from methano/diethyl ether yielding H—D-Phe-OMe.HCl as a white crystalline powder (187.4 g). TLC: Rf=0.54, silica gel, n-butanolacetic acid/water 10/1/3 v/v.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 30 min
  3. concentrationThe mixture was concentrated in vacuo
  4. customThe residue was crystallized from methano/diethyl ether

Sources & evidence

ORD record
ord-145a45c4b5a8413eb2a069e4e99e6914
Source dataset
uspto-grants-2002_08
Patent number
US06432921B1

Linked notes

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