L-Phenylalanine → N-(N-Formyl-L-alpha-aspartyl)-3-phenyl-L-alanine

HRID 1580544Notes

Reaction equation

HRID 1580544 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:13]([NH:15][C@@H:16]1[C:21](=[O:22])[O:20][C:18](=[O:19])[CH2:17]1)=[O:14]>C(O)(=O)C>[CH:13]([NH:15][C@H:16]([C:21]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:22])[CH2:17][C:18](=[O:19])[OH:20])=[O:14]

Participants

4

Reactant 2

HCID 6140L-PhenylalanineHCID 11298025N-[(3S)-Tetrahydro-2,5-dioxo-3-furanyl]formamide

Product 1

HCID 92472N-(N-Formyl-L-alpha-aspartyl)-3-phenyl-L-alanine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

Into a suitable reaction vessel at 45°-50°C., 34.6 g. (0.21 mole) of L-phenylalanine is added in about 45 minutes to a mixture of 30 g. (0.21 mole) of N-formyl-L-aspartic anhydride and 300 g. of glacial acetic acid. The resulting mixture is held for an additional 30 minutes, then cooled to 25°C. The resulting crystalline product is collected by filtration and washed with 50 g. of glacial acetic acid. The yield of N-formyl-α-L-aspartyl-L-phenylalanine is 40.5 g., m.p. 180°-182°C. TLC analysis of this product indicates no detectable β-form contamination.

Workup

  1. customat 45°-50°C.
  2. filtrationThe resulting crystalline product is collected by filtration
  3. washwashed with 50 g

Sources & evidence

ORD record
ord-6ae8c85733f5416b9ffff60920d1ff7c
Source dataset
uspto-grants-1976_01
Patent number
US03933781

Reaction notes

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