tert-butyl (2RS,4SR,5RS)-1-{2-[3-(3-(benzyloxycarbonyl)phenyl)ureido]acetyl}-5-(2-fluorophenyl)-4-(phenylsulphonyl)pyrrolidine-2-carboxylate → (2S,4R,5R)-3-{3-[2-(4-benzyl-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:51])[NH:19][CH2:20][C:21]([N:23]2[CH:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3F)[CH:26](S(C3C=CC=CC=3)(=O)=O)[CH2:25][CH:24]2[C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[O:22])[CH:14]=[CH:15][CH:16]=1)=[O:10])C1C=CC=CC=1>C(O)C.[Pd]>[CH2:9]([C@H:26]1[C@H:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:23]([C:21](=[O:22])[CH2:20][NH:19][C:18](=[O:51])[NH:17][C:13]2[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=2)[C:9]([OH:8])=[O:10])[C@H:24]([C:44]([O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[O:45])[CH2:25]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A The reaction is carried out in a way analogous to that described in Example 2A, but from 5.8 g of tert-butyl (2RS,4SR,5RS)-1-{2-[3-(3-(benzyloxycarbonyl)phenyl)ureido]acetyl}-5-(2-fluorophenyl)-4-(phenylsulphonyl)pyrrolidine-2-carboxylate and 0.6 g of 10% palladium-on-charcoal in 200 cm3 of ethanol. After treatment, there are obtained 2.85 g of (2RS,4SR,5RS)-3-{3-[2-(2-tert-butoxycarbonyl-5-(2-fluorophenyl)-4-phenylsulphonyl-1-pyrrolidinyl)2-oxoethyl]ureido}benzoic acid [Rf =0.25; eluent: methylene chloride/methanol (90/10)].
Sources & evidence
- ORD record
- ord-6d4997a6fc814640916a0eccf273e0f2
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05707991
Reaction notes
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