Hydrochloric Acid → HCID 67618491, compound

HRID 727592Notes

Reaction equation

HRID 727592 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]([C@@H:11]2[CH2:15][C@H:14]([S:16][C:17]3[C@H:18]([CH3:41])[C@@H:19]4[C@@H:36]([C@H:37]([OH:39])[CH3:38])[C:35](=[O:40])[N:20]4[C:21]=3[C:22]([O:24]CC3C=CC([N+]([O-])=O)=CC=3)=[O:23])[CH2:13][N:12]2C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)=[O:10])[CH2:3]1.[ClH:55]>O1CCCC1.O>[ClH:55].[CH3:8][C@H:6]1[NH:7][C@@H:2]([CH3:1])[CH2:3][N:4]([C:9]([C@@H:11]2[CH2:15][C@H:14]([S:16][C:17]3[C@H:18]([CH3:41])[C@@H:19]4[C@@H:36]([C@H:37]([OH:39])[CH3:38])[C:35](=[O:40])[N:20]4[C:21]=3[C:22]([OH:24])=[O:23])[CH2:13][NH:12]2)=[O:10])[CH2:5]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131720415HCID 131720415, compound

Product 1

HCID 67618491HCID 67618491, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The whole of the 4-nitrobenzyl (1R, 5S, 6S)-2-[(2S, 4S)-2-(cis-3,5-dimethyl-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 was dissolved in 4 ml of a 1:1 by volume mixture of tetrahydrofuran and water, after which 261 μl of 1N aqueous hydrochloric acid were added, and the mixture was hydrogenated by bubbling hydrogen through it at room temperature for 2 hours in the presence of 0.2 g 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 8(b), to give 27 mg of the title compound as a powder.

Workup

  1. customby bubbling hydrogen through it at room temperature for 2 hours in the presence of 0.2 g of 10% w/w palladium-on-charcoal
  2. custompurified by the same procedure

Sources & evidence

ORD record
ord-d4bb71e29af44869ad03fd055bb25749
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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