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

HRID 267309Notes

Reaction equation

HRID 267309 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 a additional 60 parts of methanol is added. The mixture then is filtered and the solid remaining is washed with additional methanol and dried. Recrystallization from methanol affords the crystalline salt of N-acetyl-D-phenylalanine and L-phenylalanine methyl ester, melting at about 170°-172° and displaying an [α]D in 0.5% water of about -33.3°.

Workup

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

Sources & evidence

ORD record
ord-62d92d790ac8463ea5cc8c9f4e4540ee
Source dataset
uspto-grants-1976_03
Patent number
US03941831

Reaction notes

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