Hydrochloric Acid → HCID 67618529, compound

HRID 362001Notes

Reaction equation

HRID 362001 reaction equation
[CH3:1][N:2]([C@H:49]1[CH2:53][CH2:52][N:51](C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)[CH2:50]1)[C:3]([C@@H:5]1[CH2:9][C@H:8]([S:10][C:11]2[C@H:12]([CH3:35])[C@@H:13]3[C@@H:30]([C@H:31]([OH:33])[CH3:32])[C:29](=[O:34])[N:14]3[C:15]=2[C:16]([O:18]CC2C=CC([N+]([O-])=O)=CC=2)=[O:17])[CH2:7][N:6]1C(OCC1C=CC([N+]([O-])=O)=CC=1)=O)=[O:4].[ClH:67]>O1CCCC1.O>[ClH:67].[CH3:1][N:2]([C@H:49]1[CH2:53][CH2:52][NH:51][CH2:50]1)[C:3]([C@@H:5]1[CH2:9][C@H:8]([S:10][C:11]2[C@H:12]([CH3:35])[C@@H:13]3[C@@H:30]([C@H:31]([OH:33])[CH3:32])[C:29](=[O:34])[N:14]3[C:15]=2[C:16]([OH:18])=[O:17])[CH2:7][NH:6]1)=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131720421HCID 131720421, compound

Product 1

HCID 67618529HCID 67618529, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

500 mg of 4-nitrobenzyl (1R, 5S, 6S)-2-{(2S, 4S)-2-(N-methyl-N-[(3S)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-3-yl]carbamoyl}-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 20 ml of a 1:1 by volume mixture of tetrahydrofuran and water, after which 0.45 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 700 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 18(b), to give 30 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 700 mg of 10% w/w palladium-on-charcoal
  2. custompurified by the same procedure

Sources & evidence

ORD record
ord-136f0b852bcc4923aa35994eea577acf
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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