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

HRID 2304337Notes

Reaction equation

HRID 2304337 reaction equation
[NH2:1][C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.S(Cl)([Cl:15])=O.[CH3:17]O>>[ClH:15].[CH3:17][O:11][C:10](=[O:12])[C@@H:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[NH2:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 71567D-Phenylalanine

Product 1

HCID 11481330methyl (2R)-2-amino-3-phenylpropanoate;hydrochlorideYield 97%

Procedure

(D)-Phenylalanine (25.0 g) was dissolved in 450 mL of methanol and 22 mL thionyl chloride were slowly added at −20° C. The mixture was refluxed for 1 h, followed by evaporation of the volatiles to give 31.2 g (97%) of the title compound as a white solid. M.p. 155-163° C.

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. customfollowed by evaporation of the volatiles

Sources & evidence

ORD record
ord-dfc69a8314294b2486593e635141cd5a
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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