Sodium Bicarbonate → HCID 23388255, compound

HRID 1839340Notes

Reaction equation

HRID 1839340 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:35](=[O:36])[N:6]2[C:7]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=3)=[O:23])=[C:8]([C:11]3[S:15][C:14]4=[C:16](SC)[N:17]=[C:18]([CH3:19])[N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].O[O:38][S:39]([O-:41])=O.[K+].[C:43](=O)([O-])O.[Na+]>C1COCC1.O>[OH:1][C@@H:2]([C@H:4]1[C:35](=[O:36])[N:6]2[C:7]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=3)=[O:23])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([S:39]([CH3:43])(=[O:41])=[O:38])[N:17]=[C:18]([CH3:19])[N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 23388225HCID 23388225, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 23388255HCID 23388255, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(5-methyl-7methylthioimidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate (315 mg) was dissolved in 6 ml of THF and 6 ml of water. To the solution was added 368 mg of OXONE (manufactured by Du Pont (E.I.) de Nemours & Co.) under ice cooling. The mixture was stirred at the same temperature for 1.5 hr. An aqueous sodium hydrogencarbonate solution was added thereto, followed by extraction with dichloromethane. The extract was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=20:1 to 10:1). Of two main components, the fraction, which had been eluted earlier, was concentrated under the reduced pressure to give 145 mg of 4-nitrobenzyl (S,5R,6S)-6-((1R)-1-hydroxyethyl)-2(7-methanesulfonyl-5-methylimidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylate.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation under the reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=20:1 to 10:1)
  5. washOf two main components, the fraction, which had been eluted earlier
  6. concentrationwas concentrated under the reduced pressure

Sources & evidence

ORD record
ord-59feb4c4ccde4612a28bea12cf10cc4e
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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