HCID 11143993, compound → 4-Nitrobenzyl (1R, 5S,6S)-2-[(3S,5S)-5-[3-(S)-(4-nitrobenzyloxycarbonyl)aminopyrrolidin-1-ylcarbonyl]-1-methylpyrrolidin-3-ylthio)-6-[1(R)-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate
Reaction equation
C(N(CC)C(C1C=CC=CC=1S([C:14]1[C@H:15]([CH3:38])[C@@H:16]2[C@@H:33]([C@H:34]([OH:36])[CH3:35])[C:32](=[O:37])[N:17]2[C:18]=1[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:20])=O)=O)C.[SH:41][C@@H:42]1[CH2:46][N:45]([CH3:47])[C@H:44]([C:48]([N:50]2[CH2:54][CH2:53][C@H:52]([NH:55][C:56]([O:58][CH2:59][C:60]3[CH:65]=[CH:64][C:63]([N+:66]([O-:68])=[O:67])=[CH:62][CH:61]=3)=[O:57])[CH2:51]2)=[O:49])[CH2:43]1>>[N+:66]([C:63]1[CH:62]=[CH:61][C:60]([CH2:59][O:58][C:56]([NH:55][C@H:52]2[CH2:53][CH2:54][N:50]([C:48]([C@H:44]3[N:45]([CH3:47])[CH2:46][C@@H:42]([S:41][C:14]4[C@H:15]([CH3:38])[C@@H:16]5[C@@H:33]([C@H:34]([OH:36])[CH3:35])[C:32](=[O:37])[N:17]5[C:18]=4[C:19]([O:21][CH2:22][C:23]4[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=4)=[O:20])[CH2:43]3)=[O:49])[CH2:51]2)=[O:57])=[CH:65][CH:64]=1)([O-:68])=[O:67]Participants
3
Reactant 2
Product 1
Procedure
Following a procedure similar to that described in Example 27(b), but using 4-nitrobenzyl (1R,5S,6S)-2-(2-diethylcarbamoylphenylsulfinyl)-1-methyl-6-[1(R)-hydroxyethyl]-1-carbapen-2-em-3-carboxylate [prepared as described in Example 27(a)] and (2S,4S)-4-mercapto-2-[3 (S)-(4-nitrobenzyloxycarbonyl)aminopyrrolidin-1-ylcarbonyl]-1-methylpyrrolidine as starting materials, in relative proportions similar to those used in that Example, the title compound was obtained as a powder in a yield of 60%.
Sources & evidence
- ORD record
- ord-55efe6a874264b33a3fdf37ad1edeb78
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05719275
Reaction notes
Loading…