L-Phenylalanine → L-Aspartyl-L-phenylalanine

HRID 483669Notes

Reaction equation

HRID 483669 reaction equation
C[O:2][C:3](=[O:13])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:5].[NH2:14][C@@H:15]1[C:20](=[O:21])[O:19][C:17](=[O:18])[CH2:16]1.N[C@H](C(O)=O)CC1C=CC=CC=1.C(N[C@@H]1C(=O)OC(=O)C1)=O>C(O)(=O)C>[NH2:14][C@H:15]([C:20]([NH:5][C@H:4]([C:3]([OH:2])=[O:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:21])[CH2:16][C:17](=[O:18])[OH:19]

Participants

6

Reactant 4

HCID 6140L-PhenylalanineHCID 736234L-Phenylalanine, methyl ester2×HCID 11298025N-[(3S)-Tetrahydro-2,5-dioxo-3-furanyl]formamideHCID 11469168(3S)-3-Aminodihydro-2,5-furandione

Product 1

HCID 93078L-Aspartyl-L-phenylalanine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In known methods for producing α-AMP, an N-protected-L-aspartic anhydride is reacted with L-phenylalanine methyl ester in an organic solvent, and then the protecting group is eliminated by a conventional method (U.S. Pat. No. 3,786,039); and addition salt of L-aspartic anhydride with a strong acid is directly reacted with L-phenylalanine methyl ester (Japanese Patent Publication No. 14,217/74); or L-phenylalanine is reacted with N-formyl-L-aspartic anhydride in glacial acetic acid, and the formyl group is eliminated from the product to give α-L-aspartyl-L-phenylalanine (hereinafter referred to as α-AP), which is then esterified with methanol (U.S. Pat. No. 3,933,781).

Workup

  1. customIn known methods for producing α-AMP

Sources & evidence

ORD record
ord-e7bb6247805f4ae2b3c50dee4fe9f06e
Source dataset
uspto-grants-1993_07
Patent number
US05225587

Reaction notes

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