Hydrochloric Acid → HCID 67618887, compound

HRID 362000Notes

Reaction equation

HRID 362000 reaction equation
[CH3:1][N:2]([CH3:54])[C@H:3]1[CH2:7][CH2:6][N:5]([C:8]([C@@H:10]2[CH2:14][C@H:13]([S:15][C:16]3[C@H:17]([CH3:40])[C@@H:18]4[C@@H:35]([C@H:36]([OH:38])[CH3:37])[C:34](=[O:39])[N:19]4[C:20]=3[C:21]([O:23]CC3C=CC([N+]([O-])=O)=CC=3)=[O:22])[CH2:12][N:11]2C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)=[O:9])[CH2:4]1.[ClH:55]>O1CCCC1.O>[ClH:55].[CH3:54][N:2]([CH3:1])[C@H:3]1[CH2:7][CH2:6][N:5]([C:8]([C@@H:10]2[CH2:14][C@H:13]([S:15][C:16]3[C@H:17]([CH3:40])[C@@H:18]4[C@@H:35]([C@H:36]([OH:38])[CH3:37])[C:34](=[O:39])[N:19]4[C:20]=3[C:21]([OH:23])=[O:22])[CH2:12][NH:11]2)=[O:9])[CH2:4]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10533194HCID 10533194, compound

Product 1

HCID 67618887HCID 67618887, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

306 mg of 4-nitrobenzyl (1R, 5S, 6S)-2-{(2S, 4S)-2-[(3S)-3-dimethylaminopyrrolidin-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 12 ml of a 2:1 by volume mixture of tetrahydrofuran and water, after which 0.38 ml of 1N aqueous hydrochloric acid was added, and the mixture was hydrogenated by bubbling hydrogen through it at room temperature for 2 hours in the presence of 600 mg of 10% w/w palladium-on-charcoal. The reaction mixture was then worked up and purified by the same procedure as described in Example 18(b), to give 19 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 600 mg of 10% w/w palladium-on-charcoal
  2. custompurified by the same procedure

Sources & evidence

ORD record
ord-4265e11571ab4e628f4006c04fb265f7
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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