Acetaldehyde → HCID 13049157, compound
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](=O)[CH3:14]>>[CH2:13]([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)[CH3:14]Participants
Procedure
According to a further embodiment of the present invention D-phenylalanine is submitted to hydrogenolysis in the presence of acetaldehyde, the resulting N-ethyl-D-phenylalanine is provided with a benzyloxycarbonyl protecting group, its 2,4,5-trichlorophenyl ester is formed, then it is condensed with L-proline. The N-benzyloxycarbonyl-N-ethyl-D-phenylalanyl-L-proline obtained is coupled by the mixed anhydride method to Nω -benzyloxycarbonyl-L-arginine lactam. The protected tripeptide lactam obtained is reduced by lithium aluminum hydride to N-benzyloxycarbonyl-N-ethyl-D-phenylalanyl-L-prolyl-Nω-benzyloxycarbonyl-L-arginine-aldehyde, the protecting groups are removed by hydrogenolysis in the presence of sulfuric acid and the resulting N-ethyl-D-phenylalanyl-L-prolyl-L-arginine-aldehyde sulfate is isolated.
Sources & evidence
- ORD record
- ord-b94d39ebdeec4c0f9bdc245f82a316e4
- Source dataset
- uspto-grants-1987_10
- Patent number
- US04703036
Reaction notes
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