Hydrochloric Acid → HCID 88319320, compound

HRID 362003Notes

Reaction equation

HRID 362003 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([C@@H:13]2[CH2:17][C@H:16]([S:18][C:19]3[C@H:20]([CH3:43])[C@@H:21]4[C@@H:38]([C@H:39]([OH:41])[CH3:40])[C:37](=[O:42])[N:22]4[C:23]=3[C:24]([O:26]CC3C=CC([N+]([O-])=O)=CC=3)=[O:25])[CH2:15][N:14]2C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)=[O:12])[CH2:6][CH2:5]1.[ClH:57]>O1CCCC1.O>[ClH:57].[F:1][CH2:2][CH2:3][N:4]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([C@@H:13]2[CH2:17][C@H:16]([S:18][C:19]3[C@H:20]([CH3:43])[C@@H:21]4[C@@H:38]([C@H:39]([OH:41])[CH3:40])[C:37](=[O:42])[N:22]4[C:23]=3[C:24]([OH:26])=[O:25])[CH2:15][NH:14]2)=[O:12])[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131720422HCID 131720422, compound

Product 1

HCID 88319320HCID 88319320, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

500 mg of 4-nitrobenzyl (1R, 5S, 6S)-2-{(2S, 4S)-2-[4-(2-fluoroethyl)-1-homopiperazinylcarbonyl]-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 1:1 by volume mixture of tetrahydrofuran and water, after which 0.62 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 500 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 15(b), to give 96 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 500 mg of 10% w/w palladium-on-charcoal
  2. custompurified by the same procedure

Sources & evidence

ORD record
ord-df6f48c5d62946e893ee08cfdfc67200
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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