1-[(4-Nitrophenyl)methyl] (2S,4S)-4-(acetylthio)-1,2-pyrrolidinedicarboxylate → 4-Acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-(3-allyloxycarbonyl-5-carbamoylphenylcarbamoyl)pyrrolidine
Reaction equation
[C:1]([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([C:23](O)=[O:24])[CH2:6]1)(=[O:3])[CH3:2].[CH2:26]([O:29][C:30]([C:32]1[CH:33]=[C:34]([CH:38]=[C:39]([NH2:41])[CH:40]=1)[C:35]([NH2:37])=[O:36])=[O:31])[CH:27]=[CH2:28]>>[C:1]([S:4][CH:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)=[O:11])[CH:7]([C:23](=[O:24])[NH:41][C:39]2[CH:38]=[C:34]([C:35](=[O:36])[NH2:37])[CH:33]=[C:32]([C:30]([O:29][CH2:26][CH:27]=[CH2:28])=[O:31])[CH:40]=2)[CH2:6]1)(=[O:3])[CH3:2]Participants
3
Procedure
(2S,4S)-4-Acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-carboxy-pyrrolidine (0.75 g) was converted to the acid chloride and reacted with 3-allyloxycarbonyl-5-aminobenzamide (0.45 g) by a similar method to that described in example 12. The crude product was subjected to chromatography on silica gel, eluting with EtOAc and giving 4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-(3-allyloxycarbonyl-5-carbamoylphenylcarbamoyl)pyrrolidine (0.58 g). Nmr (DMSO-d6): δ 1.92-2.06 (m, 1H); 2.3 (s, 3H); 2.79-2.83 (m, 1H); 3.38 (dd, 1H); 3.97-4.12 (m, 2H); 4.49 (dd, 1H); 4.83 (dt, 2H); 5.19 (dd, 2H); 5.25-5.43 (m, 2H); 5.97-6.11 (m, 1H); 7.31 (broad s, 2H); 7.54 (d, 2H); 8.04 (d, 2H); 8.12 (t, 1H); 8.26 (t, 1H); 8.31 (t, 1H); 10.0 (s, 1H).
Workup
- washeluting with EtOAc
Sources & evidence
- ORD record
- ord-f30f7c502d0640e0979310c7f168f77d
- Source dataset
- uspto-grants-1999_01
- Patent number
- US05856321
Reaction notes
Loading…