HCID 131720407, compound → HCID 22881594, compound

HRID 727584Notes

Reaction equation

HRID 727584 reaction equation
[N+](C1C=CC(COC([N:12]=[C:13]([N:15]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([C@@H:24]3[CH2:28][C@H:27]([S:29][C:30]4[C@H:31]([CH3:54])[C@@H:32]5[C@@H:49]([C@H:50]([OH:52])[CH3:51])[C:48](=[O:53])[N:33]5[C:34]=4[C:35]([O:37]CC4C=CC([N+]([O-])=O)=CC=4)=[O:36])[CH2:26][N:25]3C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)=[O:23])[CH2:17][CH2:16]2)[CH3:14])=O)=CC=1)([O-])=O>O1CCCC1.O>[C:13]([N:15]1[CH2:21][CH2:20][CH2:19][N:18]([C:22]([C@@H:24]2[CH2:28][C@H:27]([S:29][C:30]3[C@H:31]([CH3:54])[C@@H:32]4[C@@H:49]([C@H:50]([OH:52])[CH3:51])[C:48](=[O:53])[N:33]4[C:34]=3[C:35]([OH:37])=[O:36])[CH2:26][NH:25]2)=[O:23])[CH2:17][CH2:16]1)(=[NH:12])[CH3:14]

Participants

4

Reactant 1

HCID 131720407HCID 131720407, compound

Product 1

HCID 22881594HCID 22881594, compoundYield 33.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

144 mg of 4-nitrobenzyl (1R,5S,6S)-2-[(2S,4S)-2-(4-(N-4-nitrobenzyloxycarbonylacetimidoyl)homopiperazin-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 7.5 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 1.5 hours in the presence of 375 mg 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 1(b), to give 24 mg of the title compound as a powder.

Workup

  1. customby bubbling hydrogen through the solution at room temperature for 1.5 hours in the presence of 375 mg of 10% w/w palladium-on-charcoal
  2. custompurified by the same procedure

Sources & evidence

ORD record
ord-84cdb4bb2f5549f2b1aef42f762079f4
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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