HCID 131722925, compound → HCID 131722930, compound

HRID 382650Notes

Reaction equation

HRID 382650 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:33](=[O:34])[N:6]2[C:7]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)=[O:21])=[C:8]([C:10]3[N:11]4[CH:17]=[N:16][C:15]([CH2:18][OH:19])=[C:12]4[S:13][CH:14]=3)[CH2:9][C@H:5]12)[CH3:3]>ClCCl.[O-2].[O-2].[Mn+4]>[CH:18]([C:15]1[N:16]=[CH:17][N:11]2[C:10]([C:8]3[CH2:9][C@@H:5]4[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:33](=[O:34])[N:6]4[C:7]=3[C:20]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=3)=[O:21])=[CH:14][S:13][C:12]=12)=[O:19]

Participants

4

Reactant 1

HCID 131722925HCID 131722925, compound

Product 1

HCID 131722930HCID 131722930, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution 428 mg of 4-nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(7-hydroxymethylimidazo[5,1-b]thiazol-3-yl)-1-carbapen-2-em-3-carboxylate in 30 ml of dichloromethane was added 1.03 g of manganese dioxide, and the mixture was stirred at room temperature for 18 hours. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue thus obtained was washed with diethyl ether to give 202.8 mg of 4-nitrobenzyl (5R,6S)-2-(7-formylimidazo[5,1-b]thiazol-3-yl)-6-((1R)-1-hydroxyethyl)-1-carbapen-2-em-3-carboxylate.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue thus obtained
  4. washwas washed with diethyl ether

Sources & evidence

ORD record
ord-883c212a342b4257867475e8ee438a3e
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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