tert-butyl (2RS,5RS)-1-{2-[3-(3-benzyloxycarbonylphenyl)ureido]-acetyl}-5-phenylprolinate → (2RS,5RS)-3-{3-[2-(2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}benzoic acid
Reaction equation
C([O:8][C:9]([C:11]1[CH:12]=[C:13]([NH:17][C:18](=[O:41])[NH:19][CH2:20][C:21]([N:23]2[CH:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:33][CH2:32][CH:24]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:22])[CH:14]=[CH:15][CH:16]=1)=[O:10])C1C=CC=CC=1>[Pd].C(O)C>[C:28]([O:27][C:25]([CH:24]1[CH2:32][CH2:33][CH:34]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:23]1[C:21](=[O:22])[CH2:20][NH:19][C:18](=[O:41])[NH:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[C:9]([OH:10])=[O:8])=[O:26])([CH3:31])([CH3:29])[CH3:30]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
The operation is carried out in a fashion similar to that described in Example 100, but starting from 10.2 g of tert-butyl (2RS,5SR)-1-{2-[3-(3-benzyloxycarbonylphenyl)-ureido]acetyl}-5-phenylprolinate and 1 g of 5% palladium on charcoal in 300 cm3 of ethanol. After treatment, 7.1 g of (2RS,5RS)-3-{3-[2-(2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}benzoic acid, melting at 236° C., are obtained.
Sources & evidence
- ORD record
- ord-1f2c5b2ad2904ef48ab0bd6fa41eec2d
- Source dataset
- uspto-grants-1997_03
- Patent number
- US05610144
Reaction notes
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