Hydrochloric Acid → HCID 67617536, compound

HRID 362002Notes

Reaction equation

HRID 362002 reaction equation
[C:1]([CH:4]1[N:9](C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)[CH2:8][CH2:7][N:6]([C:23]([C@@H:25]2[CH2:29][C@H:28]([S:30][C:31]3[C@H:32]([CH3:55])[C@@H:33]4[C@@H:50]([C@H:51]([OH:53])[CH3:52])[C:49](=[O:54])[N:34]4[C:35]=3[C:36]([O:38]CC3C=CC([N+]([O-])=O)=CC=3)=[O:37])[CH2:27][N:26]2C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)=[O:24])[CH2:5]1)(=[O:3])[NH2:2].[ClH:69]>O1CCCC1.O>[ClH:69].[C:1]([CH:4]1[NH:9][CH2:8][CH2:7][N:6]([C:23]([C@@H:25]2[CH2:29][C@H:28]([S:30][C:31]3[C@H:32]([CH3:55])[C@@H:33]4[C@@H:50]([C@H:51]([OH:53])[CH3:52])[C:49](=[O:54])[N:34]4[C:35]=3[C:36]([OH:38])=[O:37])[CH2:27][NH:26]2)=[O:24])[CH2:5]1)(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131721108HCID 131721108, compound

Product 1

HCID 67617536HCID 67617536, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.33 g of 4-nitrobenzyl (1R, 5S, 6S)-2-{(2S, 4S)-2-[3-carbamoyl-4-(4-nitrobenzyloxycarbonyl)-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] were dissolved in 25 ml of a 1:1 by volume mixture of tetrahydrofuran and water, after which 2.7 ml 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 2.33 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 7(b), to give 160 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 2.33 g of 10% w/w palladium-on-charcoal
  2. custompurified by the same procedure

Sources & evidence

ORD record
ord-abf2e2a24d604cdc839045b4f2d53b66
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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