Phosphate → HCID 9819016, compound

HRID 382606Notes

Reaction equation

HRID 382606 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:32](=[O:33])[N:6]2[C:7]([C:19]([O:21]CC3C=CC([N+]([O-])=O)=CC=3)=[O:20])=[C:8]([C:11]3[S:15][C:14]4=[CH:16][N:17]=[CH:18][N:13]4[CH:12]=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:32](=[O:33])[N:6]2[C:7]([C:19]([OH:21])=[O:20])=[C:8]([C:11]3[S:15][C:14]4=[CH:16][N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

5

Reactant 2

HCID 1061PhosphateHCID 12069976HCID 12069976, compound

Product 1

HCID 9819016HCID 9819016, compoundYield 19.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.70 g of 4-nitro-benzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylate in 90 ml of THF and 50 ml of 1/15 M phosphate buffer (pH 6.8) was added 7.0 g of 10% Pd-C. The reactor was purged with hydrogen, and the reaction mixture was stirred at room temperature for 4 hours. The catalyst was removed by filtration with Celite, and washed with 300 ml of water and 50 ml of THF. The filtrate was diluted with 200 ml of ethyl acetate and washed with water. The aqueous layer was separated from the filtrate, and concentrated under reduced pressure to a volume of about 300 ml, which was purified by column chromatography on DIAION HP-20. The fraction containing the aimed product was concentrated under reduced pressure, crystallized from 12 ml of water to give 656 mg of the title compound.

Workup

  1. customThe reactor was purged with hydrogen
  2. customThe catalyst was removed by filtration with Celite
  3. washwashed with 300 ml of water and 50 ml of THF
  4. additionThe filtrate was diluted with 200 ml of ethyl acetate
  5. washwashed with water
  6. customThe aqueous layer was separated from the filtrate
  7. concentrationconcentrated under reduced pressure to a volume of about 300 ml, which
  8. customwas purified by column chromatography on DIAION HP-20
  9. additionThe fraction containing the aimed product
  10. concentrationwas concentrated under reduced pressure
  11. customcrystallized from 12 ml of water

Sources & evidence

ORD record
ord-b2df399b34474ac48190403a3584f427
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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