Phosphate → (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-3-yl)-1-carbapen-2-em-3-carboxylic Acid

HRID 382624Notes

Reaction equation

HRID 382624 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:31](=[O:32])[N:6]2[C:7]([C:18]([O:20]CC3C=CC([N+]([O-])=O)=CC=3)=[O:19])=[C:8]([C:10]3[N:11]4[CH:17]=[N:16][CH:15]=[C:12]4[S:13][CH:14]=3)[CH2:9][C@H:5]12)[CH3:3].P([O-])([O-])([O-])=O>C1COCC1.[Pd]>[OH:1][C@@H:2]([C@H:4]1[C:31](=[O:32])[N:6]2[C:7]([C:18]([OH:20])=[O:19])=[C:8]([C:10]3[N:11]4[CH:17]=[N:16][CH:15]=[C:12]4[S:13][CH:14]=3)[CH2:9][C@H:5]12)[CH3:3]

Participants

5

Reactant 2

HCID 1061PhosphateHCID 1317229034-nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-3-yl)-1-carbapen-2-em-3-carboxylate

Product 1

HCID 12070052(5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-3-yl)-1-carbapen-2-em-3-carboxylic AcidYield 23%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 203 mg of 4-nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-3-yl)-1-carbapen-2-em-3-carboxylate in 4 ml of THF and 4 ml of 1/15 M phosphate buffer (pH 6.8) was added 152 mg of 10% Pd-C. The reactor was purged with hydrogen, the reaction mixture was stirred at room temperature for 1 hour. The catalyst was collected by filtration on Celite, and washed with water. The filtrate was washed with ethyl acetate, and then the aqueous layer was purified by column chromatography on DIAION HP-20, followed by crystallization form 1 ml of water to give 32.8 mg of the title compound.

Workup

  1. customThe reactor was purged with hydrogen
  2. filtrationThe catalyst was collected by filtration on Celite
  3. washwashed with water
  4. washThe filtrate was washed with ethyl acetate
  5. customthe aqueous layer was purified by column chromatography on DIAION HP-20
  6. customfollowed by crystallization
  7. customform 1 ml of water

Sources & evidence

ORD record
ord-7e9a2aefd6774d50a65dfc392bfcde4b
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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