Methanol → Methyl L-phenylalaninate hydrochloride

HRID 981771Notes

Reaction equation

HRID 981771 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 in vacuo 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 in vacuo
  3. customto produce a white solid

Sources & evidence

ORD record
ord-f4092f7a9c4642838f7175f6b19df42e
Source dataset
uspto-grants-1991_02
Patent number
US04992552

Reaction notes

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