Methanol → 4-Chloro-L-phenylalanine methyl ester hydrochloride

HRID 246885Notes

Reaction equation

HRID 246885 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:17]=[CH:16][C:9]([CH2:10][C@@H:11]([C:13]([OH:15])=[O:14])[NH2:12])=[CH:8][CH:7]=1.[CH3:18]O>>[ClH:3].[CH3:18][O:14][C:13](=[O:15])[C@H:11]([CH2:10][C:9]1[CH:8]=[CH:7][C:6]([Cl:5])=[CH:17][CH:16]=1)[NH2:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 7361904-Chloro-L-phenylalanine

Product 1

HCID 236191574-Chloro-L-phenylalanine methyl ester hydrochloride

Procedure

0.14 mol (10 ml, 16.5 grams) of thionyl chloride were dropped at -5° C. into 100 ml of methanol. After addition of 0.11 mole (22 grams) of 4-chlorophenylalanine the mixture was heated under reflux for 15 hours. After drawing off the solvent the white residue was dried in a high vacuum.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. customwas dried in a high vacuum

Sources & evidence

ORD record
ord-78935f969b6749c4b96021cbd113fd32
Source dataset
uspto-grants-1987_11
Patent number
US04704464

Reaction notes

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