HCID 178462276, compound → HCID 178462290, compound

HRID 382610Notes

Reaction equation

HRID 382610 reaction equation
[I-].[OH:2][C@@H:3]([C@H:5]1[C:34](=[O:35])[N:7]2[C:8]([C:21]([O:23]CC3C=CC([N+]([O-])=O)=CC=3)=[O:22])=[C:9]([C:12]3[S:16][C:15]4=[CH:17][N:18]([CH3:20])[CH:19]=[N+:14]4[CH:13]=3)[C@H:10]([CH3:11])[C@H:6]12)[CH3:4]>C1COCC1.P([O-])([O-])([O-])=O.[Pd]>[OH:2][C@@H:3]([C@H:5]1[C:34](=[O:35])[N:7]2[C:8]([C:21]([O-:23])=[O:22])=[C:9]([C:12]3[S:16][C:15]4=[CH:17][N:18]([CH3:20])[CH:19]=[N+:14]4[CH:13]=3)[C@H:10]([CH3:11])[C@H:6]12)[CH3:4]

Participants

5

Reactant 1

HCID 178462276HCID 178462276, compound

Product 1

HCID 178462290HCID 178462290, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 1061PhosphateSolventHCID 8028TetrahydrofuranSolvent

Procedure

The total volume of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(6-methylimidazo[5,1-b]thiazolium-2-yl)-1-carbapen-2-em-3-carboxylate iodide was dissolved in a mixture of 2 ml of THF and 2 ml of {fraction (1/15)} M phosphate buffer (pH 6.8), 77 mg of 10% Pd-C was added. The reactor was purged with hydrogen, and the reaction mixture was stirred at room temperature for 5 hours. The catalyst was collected by filtration with Celite and washed with water. The filtrate was washed with 20 ml of ethyl acetate, and purified by column chromatography on DIAION HP-20 to give 14.1 mg of the title compound.

Workup

  1. additionwas added
  2. customThe reactor was purged with hydrogen
  3. filtrationThe catalyst was collected by filtration with Celite
  4. washwashed with water
  5. washThe filtrate was washed with 20 ml of ethyl acetate
  6. custompurified by column chromatography on DIAION HP-20

Sources & evidence

ORD record
ord-c778a048858444069cd487e2e08653d6
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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