Trisodium Phosphate → Sodium (1s,5r,6s)-2-(7-acetylimidazo[5,1-b]thiazol-2-yl)-6-((1r)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

HRID 382651Notes

Reaction equation

HRID 382651 reaction equation
[C:1]([C:4]1[N:5]=[CH:6][N:7]2[CH:11]=[C:10]([C:12]3[C@H:13]([CH3:36])[C@@H:14]4[C@@H:31]([C@H:32]([OH:34])[CH3:33])[C:30](=[O:35])[N:15]4[C:16]=3[C:17]([O:19]CC3C=CC([N+]([O-])=O)=CC=3)=[O:18])[S:9][C:8]=12)(=[O:3])[CH3:2].P([O-])([O-])([O-])=O.[Na+:42].[Na+].[Na+]>C1COCC1.[Pd]>[C:1]([C:4]1[N:5]=[CH:6][N:7]2[CH:11]=[C:10]([C:12]3[C@H:13]([CH3:36])[C@@H:14]4[C@@H:31]([C@H:32]([OH:34])[CH3:33])[C:30](=[O:35])[N:15]4[C:16]=3[C:17]([O-:19])=[O:18])[S:9][C:8]=12)(=[O:3])[CH3:2].[Na+:42]

Participants

5

Reactant 2

HCID 24243Trisodium PhosphateHCID 233882054-Nitrobenzyl (1s,5r,6s)-2-(7-acetylimidazo[5,1-b]thiazol-2-yl)-6-((1r)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

Product 1

HCID 23698608Sodium (1s,5r,6s)-2-(7-acetylimidazo[5,1-b]thiazol-2-yl)-6-((1r)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 98.2 mg of 4-nitrobenzyl (1S,5R,6S)-2-(7-acetylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate in 5.8 ml of THF and 5.8 ml of 1/15 M sodium phosphate buffer (pH 6.6) was added 98 mg of 10% Pd-C. The reactor was purged with hydrogen, and the reaction mixture was stirred at room temperature for 2 hours. The catalyst was removed by filtration through Celite, and washed with water. The filtrate was adjusted to pH 6.5 with an aqueous sodium hydrogen carbonate solution, washed with ethyl acetate, and the aqueous layer was purified by column chromatography on DIAION HP-20 (20% methanol in water) to give 38.1 mg of the title compound.

Workup

  1. customThe reactor was purged with hydrogen
  2. customThe catalyst was removed by filtration through Celite
  3. washwashed with water
  4. washwashed with ethyl acetate
  5. customthe aqueous layer was purified by column chromatography on DIAION HP-20 (20% methanol in water)

Sources & evidence

ORD record
ord-8f9c47fea1854c2e8acd853e0af714a9
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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