Methanol → Methyl L-phenylalaninate hydrochloride

HRID 249422

Reaction equation

HRID 249422 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.[CH3:17]O>>[ClH:3].[CH3:17][O:15][C:14](=[O:16])[C@H:6]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:5]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 6140L-PhenylalanineHCID 24386Thionyl Chloride2×

Product 1

HCID 75736Methyl L-phenylalaninate hydrochlorideYield 99.4%

Procedure

Thionyl chloride (14 mL, 0.19 mol) was slowly added to a vigorously stirred -5° C. suspension of L-phenylalanine (26.28 g, 0.159 mol) in methanol (250 mL). After the addition of thionyl chloride was complete, the resulting homogeneous solution was allowed to warm to room temperature and was left stirring overnight. The reaction solvent was removed invacuo to produce a white solid. This solid was redissolved in methanol (100 mL) and the resulting solution was reconcentrated in vacuo to produce the product L-phenylalanine methyl ester hydrochloride (mp 158°-159° C., 34.10 g, 0.158 mol, 99.4%). A sample of this material was converted to the N-trifluoroacetylisopropyl ester using standard procedures. The resulting ester was found to contain 0.088% of the D-isomer by gc analysis on a Chirasil-Val™ chiral gc column (obtained from Applied Science). The 1H NMR of this synthetic material was identical with that of a commercial sample.

Workup

  1. waitwas left
  2. customThe reaction solvent was removed invacuo
  3. customto produce a white solid

Sources & evidence

ORD record
ord-2d06d0eeb0e144d1bffd72c787447419
Source dataset
uspto-grants-1993_05
Patent number
US05214145

Linked notes

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