Sodium Thiosulfate → HCID 23388253, compound

HRID 1839345Notes

Reaction equation

HRID 1839345 reaction equation
[CH3:1][S:2][C:3]1[N:10]2[C:6]([S:7][C:8]([C:11]3[C@H:12]([CH3:35])[C@@H:13]4[C@@H:30]([C@H:31]([OH:33])[CH3:32])[C:29](=[O:34])[N:14]4[C:15]=3[C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=3)=[O:17])=[CH:9]2)=[C:5]([S:36][CH3:37])[N:4]=1.ClC1C=CC=C(C(OO)=[O:46])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[OH:33][C@@H:31]([C@H:30]1[C:29](=[O:34])[N:14]2[C:15]([C:16]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=3)=[O:17])=[C:11]([C:8]3[S:7][C:6]4=[C:5]([S:36]([CH3:37])=[O:46])[N:4]=[C:3]([S:2][CH3:1])[N:10]4[CH:9]=3)[C@H:12]([CH3:35])[C@H:13]12)[CH3:32]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 23388194HCID 23388194, compound

Product 1

HCID 23388253HCID 23388253, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Nitrobenzyl (1S,5R,6S)-2-[5,7-bis(methylthio)imidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate (140 mg) was dissolved in 2.5 ml, of dichloromethane. m-Chloroperbenzoic acid (56 mg) was added to the solution. The mixture was stirred at room temperature for 15 min. An aqueous sodium thiosulfate solution (56 ml) was added thereto, followed by separation. The organic layer was washed with 10 ml of a semisaturated aqueous sodium hydrogencarbonate solution and 10 ml of semisaturated brine and then 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 give 97 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(7-methanesulfinyl-5-methylthioimidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylate (a mixture of diastereomers).

Workup

  1. customfollowed by separation
  2. washThe organic layer was washed with 10 ml of a semisaturated aqueous sodium hydrogencarbonate solution and 10 ml of semisaturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-221599567e1648e083726cf25b69d243
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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