Phosphate → HCID 178462295, compound

HRID 382615Notes

Reaction equation

HRID 382615 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:33](=[O:34])[N:6]2[C:7]([C:20]([O:22]CC3C=CC([N+]([O-])=O)=CC=3)=[O:21])=[C:8]([C:11]3[N+:12]4[C:13](=[CH:16][N:17]([CH3:19])[CH:18]=4)[S:14][CH:15]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].P([O-])([O-])([O-])=O>C1COCC1.[Pd]>[OH:1][C@@H:2]([C@H:4]1[C:33](=[O:34])[N:6]2[C:7]([C:20]([O-:22])=[O:21])=[C:8]([C:11]3[N+:12]4[C:13](=[CH:16][N:17]([CH3:19])[CH:18]=4)[S:14][CH:15]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

5

Reactant 2

HCID 1061PhosphateHCID 178462279HCID 178462279, compound

Product 1

HCID 178462295HCID 178462295, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 60.5 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(6-methylimidazo[5,1-b]thiazolium-3-yl)-1-carbapen-2-em-3-carboxylate in 1.8 ml of THF and 1.8 ml of {fraction (1/15)} M phosphate buffer (pH 6.8) was added 71 mg of 10% Pd-C. The reactor was purged with hydrogen, and the reaction mixture was stirred at room temperature for 3.5 hours. The catalyst was collected by filtration through Celite, and washed with water. The filtrate was washed with 20 ml of ethyl acetate, and purified by column chromatography on DIAION HP-20 and on COSMOSEAL40C18-PREP (water:methanol=20:1) to give 8.3 mg of the title compound.

Workup

  1. customThe reactor was purged with hydrogen
  2. filtrationThe catalyst was collected by filtration through Celite
  3. washwashed with water
  4. washThe filtrate was washed with 20 ml of ethyl acetate
  5. custompurified by column chromatography on DIAION HP-20 and on COSMOSEAL40C18-PREP (water:methanol=20:1)

Sources & evidence

ORD record
ord-0ed731562b964f56a37957fd5539ea79
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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