HCID 23388249, compound → HCID 23388210, compound

HRID 1839343Notes

Reaction equation

HRID 1839343 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]([CH2:20][OH:21])[N:17]=[C:18]([CH3:19])[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:20]([C:16]1[N:17]=[C:18]([CH3:19])[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:35](=[O:36])[N:6]4[C:7]=3[C:22]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=3)=[O:23])[S:15][C:14]=12)=[O:21]

Participants

4

Reactant 1

HCID 23388249HCID 23388249, compound

Product 1

HCID 23388210HCID 23388210, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Nitrobenzyl (1S,5R,6S)-6((1R)-1-Hydroxyethyl)-2-(7-hydroxymethyl-5-methylimidazo-[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylate (279 mg) was dissolved in 30 ml of dichloromethane. Manganese dioxide (500 mg) was added to the solution. The mixture was stirred at room temperature for 14 hr. The reaction solution was filtered. The filtrate was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel to give 89 mg of 4-nitrobenzyl (1S,5R,6S)-2-(7-formyl-5-methylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationThe filtrate was concentrated under the reduced pressure
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f2ad1a07a49d43bd9a592a981461db21
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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