Ethanol → Benzeneacetic acid, alpha-amino-, ethyl ester, hydrochloride (1:1), (alphaR)-

HRID 1169007Notes

Reaction equation

HRID 1169007 reaction equation
O=S(Cl)[Cl:3].[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.[CH3:16][CH2:17]O>>[NH2:15][C@@H:11]([C:12]([O:14][CH2:16][CH3:17])=[O:13])[C:8]1[CH:7]=[CH:6][CH:5]=[CH:10][CH:9]=1.[ClH:3]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 70134Phenylglycine, D-

Product 1

HCID 20833765Benzeneacetic acid, alpha-amino-, ethyl ester, hydrochloride (1:1), (alphaR)-

Procedure

SOCl2 (4.3 ml) was added to an EtOH suspension (150 ml) of D-phenylglycine (8.00 g) at −50° C. The cooling of the reaction was stopped and then stirred for 71 hours at room temperature. After concentrating the reaction mixture under reduced pressure, Et2O was added to the crude crystals and then filtered to obtain the D-Phg-OEt hydrochloride.

Workup

  1. temperatureThe cooling of the reaction
  2. concentrationAfter concentrating the reaction mixture under reduced pressure, Et2O
  3. additionwas added to the crude crystals
  4. filtrationfiltered

Sources & evidence

ORD record
ord-54701e8748d243f9b9bb90819807026b
Source dataset
uspto-grants-2003_09
Patent number
US06627732B1

Reaction notes

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