DL-Phenylalanine, methyl ester → (-)-N-Acetylphenylalanine

HRID 1576907Notes

Reaction equation

HRID 1576907 reaction equation
[C:1]([NH:4][C@@H:5]([C:13]([OH:15])=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[CH3:16][O:17][C:18](=[O:28])[CH:19]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH2:20]>CO>[C:1]([NH:4][C@@H:5]([C:13]([OH:15])=[O:14])[CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)(=[O:3])[CH3:2].[CH3:16][O:17][C:18](=[O:28])[C@H:19]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH2:20]

Participants

5

Reactant 2

HCID 75737DL-Phenylalanine, methyl esterHCID 101184(-)-N-Acetylphenylalanine

Product 2

HCID 101184(-)-N-AcetylphenylalanineHCID 736234L-Phenylalanine, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

10.35 Parts of N-acetyl-D-phenylalanine is dissolved in 40 parts of methanol, then treated with 17.9 parts of DL-phenylalanine methyl ester. A precipitate forms immediately and an additional 60 parts of methanol is added. The mixture then is filtered and the solid remaining is washed with additional methanol and dried to yield the crude salt of N-acetyl-D-phenylalanine and L-phenylalanine methyl ester.

Workup

  1. filtrationThe mixture then is filtered
  2. washthe solid remaining is washed with additional methanol
  3. customdried

Sources & evidence

ORD record
ord-1c1ff4a387c240018ba59bdc50d10a83
Source dataset
uspto-grants-1976_09
Patent number
US03983162

Reaction notes

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