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

HRID 1633387Notes

Reaction equation

HRID 1633387 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 chromotography on silica gel to give N-acetoacetyl-α-L-aspartyl-L-phenylalanine methyl ester, mp 118.5°-121° C. which 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 chromotography on silica gel

Sources & evidence

ORD record
ord-ca758b54f2b2458ea17329fa4ed71fce
Source dataset
uspto-grants-1984_10
Patent number
US04480112

Reaction notes

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