Methanol → (S)-(+)-2-Phenylglycine methyl ester hydrochloride

HRID 2392830Notes

Reaction equation

HRID 2392830 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C@@H:7]([NH2:11])[C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.S(Cl)([Cl:14])=O.[CH3:16]O>>[CH3:16][O:9][C:8]([C@@H:7]([NH2:11])[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)=[O:10].[ClH:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 70134Phenylglycine, D-

Product 1

HCID 11217910(S)-(+)-2-Phenylglycine methyl ester hydrochlorideYield 100%

Procedure

To a stirred solution of D-phenylglycine (11) (20 g, 132 mmol) in methanol (100 ml) at -10° C. was added thionyl chloride (10.62 ml, 146 mmol) and the solution was refluxed for 2 hours. After concentration in vacuo the product was recrystallised from methanol-diethyl ether mixture to give the title compound (12) (26.6 g, 100%); δH (D2O; 200 MHz) 2.95-3.18 (2H, m, CH2CH), 3.62 (3H, s, CH3), 4.21 (1H, dd, J=6.1 and 7.4, CH2CH), 4.59 (2H, s, NH2), 7.06-7.27 (5H, m, ArCH).

Workup

  1. temperaturethe solution was refluxed for 2 hours
  2. concentrationAfter concentration in vacuo the product
  3. customwas recrystallised from methanol-diethyl ether mixture

Sources & evidence

ORD record
ord-fae73ae90d304974b7b6121af7c2d8d9
Source dataset
uspto-grants-1998_09
Patent number
US05801249

Reaction notes

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