HCID 70150416, compound → HCID 131722927, compound

HRID 382648Notes

Reaction equation

HRID 382648 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:34](=[O:35])[N:6]2[C:7]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)=[O:22])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([CH2:19][OH:20])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]>ClCCl.[O-2].[O-2].[Mn+4]>[CH:19]([C:16]1[N:17]=[CH:18][N:13]2[CH:12]=[C:11]([C:8]3[C@H:9]([CH3:10])[C@@H:5]4[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:34](=[O:35])[N:6]4[C:7]=3[C:21]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[CH:29][CH:30]=3)=[O:22])[S:15][C:14]=12)=[O:20]

Participants

4

Reactant 1

HCID 70150416HCID 70150416, compound

Product 1

HCID 131722927HCID 131722927, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 183.0 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(7-hydroxymethylimidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylate in 15 ml of dichloromethane 15 ml was added 596.7 mg of manganese dioxide, and the mixture was stirred at room temperature for 38 hours. The catalyst was removed by filtration on Celite, and the filtrate was removed under reduced pressure. The residue thus obtained was purified by column chromatography on silica gel (ethyl acetate:methanol=9:1) to give 127 mg of 127 mg of 4-nitrobenzyl (1S,5R,6S)-2-(7-formylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate.

Workup

  1. customThe catalyst was removed by filtration on Celite
  2. customthe filtrate was removed under reduced pressure
  3. customThe residue thus obtained
  4. customwas purified by column chromatography on silica gel (ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-30e7d747df8b4870a9d07c1e36adbf11
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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