Hydrochloric Acid → HCID 131721109, compound

HRID 362004Notes

Reaction equation

HRID 362004 reaction equation
[N:1]1([C@H:6]2[CH2:10][CH2:9][N:8]([C:11]([C@@H:13]3[CH2:17][C@H:16]([S:18][C:19]4[C@H:20]([CH3:43])[C@@H:21]5[C@@H:38]([C@H:39]([OH:41])[CH3:40])[C:37](=[O:42])[N:22]5[C:23]=4[C:24]([O:26]CC4C=CC([N+]([O-])=O)=CC=4)=[O:25])[CH2:15][N:14]3C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)=[O:12])[CH2:7]2)[CH:5]=[N:4][CH:3]=[N:2]1.[ClH:57]>O1CCCC1.O>[ClH:57].[N:1]1([C@H:6]2[CH2:10][CH2:9][N:8]([C:11]([C@@H:13]3[CH2:17][C@H:16]([S:18][C:19]4[C@H:20]([CH3:43])[C@@H:21]5[C@@H:38]([C@H:39]([OH:41])[CH3:40])[C:37](=[O:42])[N:22]5[C:23]=4[C:24]([OH:26])=[O:25])[CH2:15][NH:14]3)=[O:12])[CH2:7]2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131721111HCID 131721111, compound

Product 1

HCID 131721109HCID 131721109, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

528 mg of 4-nitrobenzyl (1R, 5S, 6S)-2-{(2S, 4S)-2-[(3S)-3-(1,2,4-triazol-1-yl)pyrrolidin-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 10 ml of a 1:1 by volume mixture of tetrahydrofuran and water, after which 0.63 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 1 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 18(b), to give 85 m of the title compound, as a powder.

Workup

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

Sources & evidence

ORD record
ord-58d31d76d774490b9dc1a12272e6d3de
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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