Diketene → N-acetoacetyl-L-aspartyl-L-phenylalanine methyl ester

HRID 1583899Notes

Reaction equation

HRID 1583899 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[CH3:7][O:8][C:9](=[O:27])[C@H:10]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:11][C:12](=[O:19])[C@H:13]([CH2:15][C:16](=[O:18])[OH:17])[NH2:14]>O1CCCC1>[CH3:7][O:8][C:9](=[O:27])[C@H:10]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[NH:11][C:12](=[O:19])[C@H:13]([CH2:15][C:16](=[O:17])[OH:18])[NH:14][C:4](=[O:5])[CH2:3][C:2]([CH3:1])=[O:6]

Participants

4

Reactant 2

HCID 12661Diketene2×HCID 134601Aspartame

Product 1

HCID 13334676N-acetoacetyl-L-aspartyl-L-phenylalanine methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.5 parts of diketene were added dropwise to a stirred suspension of 14.7 parts α-L-aspartyl-L-phenylalanine methyl ester in 400 parts by volume of tetrahydrofuran and stirred for 20 hours at ambient temperatures. An additional 4.2 parts of diketene was added. After 18 hours, the solvent was removed under vacuum and the residue was purified by chromatography on silica gel to give N-acetoacetyl-α-L-aspartyl-L-phenylalanine methyl ester, mp. 118.5°-121° C. whch eluted in a 10:90:0.1 ethanol: methylene chloride:acetic acid mixture.

Workup

  1. waitAfter 18 hours
  2. customthe solvent was removed under vacuum
  3. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7e2e6dd49f7946f59ccd20533b098cae
Source dataset
uspto-grants-1985_11
Patent number
US04555362

Reaction notes

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