HCID 131720410, compound → (1R,5S,6S)-2-{(2S,4S)-2-[(3S)-4-Formimidoyl-3-methylpiperazin-1-ylcarbonyl]pyrrolidin-4-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acid

HRID 727587Notes

Reaction equation

HRID 727587 reaction equation
[N+](C1C=CC(COC([N:12]=[CH:13][N:14]2[CH2:19][CH2:18][N:17]([C:20]([C@@H:22]3[CH2:26][C@H:25]([S:27][C:28]4[C@H:29]([CH3:52])[C@@H:30]5[C@@H:47]([C@H:48]([OH:50])[CH3:49])[C:46](=[O:51])[N:31]5[C:32]=4[C:33]([O:35]CC4C=CC([N+]([O-])=O)=CC=4)=[O:34])[CH2:24][N:23]3C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)=[O:21])[CH2:16][C@@H:15]2[CH3:66])=O)=CC=1)([O-])=O>O1CCCC1.O>[CH:13]([N:14]1[CH2:19][CH2:18][N:17]([C:20]([C@@H:22]2[CH2:26][C@H:25]([S:27][C:28]3[C@H:29]([CH3:52])[C@@H:30]4[C@@H:47]([C@H:48]([OH:50])[CH3:49])[C:46](=[O:51])[N:31]4[C:32]=3[C:33]([OH:35])=[O:34])[CH2:24][NH:23]2)=[O:21])[CH2:16][C@@H:15]1[CH3:66])=[NH:12]

Participants

4

Reactant 1

HCID 131720410HCID 131720410, compound

Product 1

HCID 22881580(1R,5S,6S)-2-{(2S,4S)-2-[(3S)-4-Formimidoyl-3-methylpiperazin-1-ylcarbonyl]pyrrolidin-4-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acidYield 37.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

87 mg of 4-nitrobenzyl (1R,5S,6S)-2-{(2S,4S)-2-[(3S)-4-(N-4-nitrobenzyloxycarbonylformimidoyl)-3-methylpiperazin-1-ylcarbonyl]-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 4.5 ml of a 2:1 by volume mixture of tetrahydrofuran and water, and were hydrogenated by bubbling hydrogen through the solution at room temperature for 2 hours in the presence of 220 mg of 10% w/w palladium-on-charcoal. The reaction mixture was then worked up and purified by the same procedure as that described in Example 1(b), to give 16 mg of the title compound, as a powder.

Workup

  1. customby bubbling hydrogen through the solution at room temperature for 2 hours in the presence of 220 mg of 10% w/w palladium-on-charcoal
  2. custompurified by the same procedure as

Sources & evidence

ORD record
ord-46058b30dd4f4d61bd3f4352827f818b
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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