Phosphate → (1S,5R,6S)-2-(3,6-dimethylimidazo[5,1-b]thiazolium-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

HRID 382622Notes

Reaction equation

HRID 382622 reaction equation
[I-].[CH3:2][C:3]1[N+:4]2[C:5](=[CH:33][N:34]([CH3:36])[CH:35]=2)[S:6][C:7]=1[C:8]1[C@H:9]([CH3:32])[C@@H:10]2[C@@H:27]([C@H:28]([OH:30])[CH3:29])[C:26](=[O:31])[N:11]2[C:12]=1[C:13]([O:15]CC1C=CC([N+]([O-])=O)=CC=1)=[O:14].P([O-])([O-])([O-])=O>C1COCC1.[Pd]>[CH3:2][C:3]1[N+:4]2[C:5](=[CH:33][N:34]([CH3:36])[CH:35]=2)[S:6][C:7]=1[C:8]1[C@H:9]([CH3:32])[C@@H:10]2[C@@H:27]([C@H:28]([OH:30])[CH3:29])[C:26](=[O:31])[N:11]2[C:12]=1[C:13]([O-:15])=[O:14]

Participants

5

Reactant 2

HCID 1061PhosphateHCID 178422144HCID 178422144, compound

Product 1

HCID 178422146(1S,5R,6S)-2-(3,6-dimethylimidazo[5,1-b]thiazolium-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylateYield 33%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 89.1 mg of 4-nitrobenzyl (1S,5R,6S)-2-(3,6-dimethylimidazo[5,1-b]thiazolium-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate iodide in 2 ml of THF and 2 ml of {fraction (1/15)} M phosphate buffer (pH 6.8) was added 102.7 mg of 10% Pd-C. The reactor was purged with hydrogen, the reaction mixture was stirred at room temperature for 5 hours. The catalyst was collected by filtration, and washed with water. The filtrate was diluted with 20 ml of ethyl acetate 20 ml, separated, and the organic layer was further washed with water. The combined aqueous layer was concentrated under reduced pressure to a volume of about 30 ml. The concentrate was purified by column chromatography on DIAION HP-20 to give 17.0 mg of the title compound.

Workup

  1. customThe reactor was purged with hydrogen
  2. filtrationThe catalyst was collected by filtration
  3. washwashed with water
  4. additionThe filtrate was diluted with 20 ml of ethyl acetate 20 ml
  5. customseparated
  6. washthe organic layer was further washed with water
  7. concentrationThe combined aqueous layer was concentrated under reduced pressure to a volume of about 30 ml
  8. customThe concentrate was purified by column chromatography on DIAION HP-20

Sources & evidence

ORD record
ord-f9849c8510b14960ad4d8562938b78d0
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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