HCID 131720424, compound → (1R, 5S, 6S)-2-[(2S, 4S)-2-(3-Carboxy-1-piperazinylcarbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acid

HRID 727605Notes

Reaction equation

HRID 727605 reaction equation
[N+](C1C=CC(C[O:9][C:10]([CH:12]2[N:17](C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:16][CH2:15][N:14]([C:31]([C@@H:33]3[CH2:37][C@H:36]([S:38][C:39]4[C@H:40]([CH3:63])[C@@H:41]5[C@@H:58]([C@H:59]([OH:61])[CH3:60])[C:57](=[O:62])[N:42]5[C:43]=4[C:44]([O:46]CC4C=CC([N+]([O-])=O)=CC=4)=[O:45])[CH2:35][N:34]3C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)=[O:32])[CH2:13]2)=[O:11])=CC=1)([O-])=O>O1CCCC1.O>[C:10]([CH:12]1[NH:17][CH2:16][CH2:15][N:14]([C:31]([C@@H:33]2[CH2:37][C@H:36]([S:38][C:39]3[C@H:40]([CH3:63])[C@@H:41]4[C@@H:58]([C@H:59]([OH:61])[CH3:60])[C:57](=[O:62])[N:42]4[C:43]=3[C:44]([OH:46])=[O:45])[CH2:35][NH:34]2)=[O:32])[CH2:13]1)([OH:11])=[O:9]

Participants

4

Reactant 1

HCID 131720424HCID 131720424, compound

Product 1

HCID 67618232(1R, 5S, 6S)-2-[(2S, 4S)-2-(3-Carboxy-1-piperazinylcarbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

160 mg of 4-nitrobenzyl (1R, 5S, 6S)-2-{(2S, 4S)-2-[3-(4-nitrobenzyloxycarbonyl)-4-(4-nitrobenzyloxycarbonyl)-1-piperazinylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate [prepared as described in step (a) above] were dissolved in 3 ml of a 1:1 by volume mixture of tetrahydrofuran and water, and the mixture was hydrogenated by bubbling hydrogen through it at room temperature for 2 hours in the presence of 160 ml of 10% w/w palladium-on-charcoal. At the end of this time, the reaction mixture was worked up and purified by the same procedure as described in Example 7(b), to give 35 ml of the title compound, as a powder.

Workup

  1. customby bubbling hydrogen through it at room temperature for 2 hours in the presence of 160 ml of 10% w/w palladium-on-charcoal
  2. custompurified by the same procedure

Sources & evidence

ORD record
ord-810b114aa9af4b9dae9f8c9078d5fd91
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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