Methyl morpholine oxide → allyl(1R,5S,6S)-2-((3S,5S)-1-allyloxycarbonyl-5-formylpyrrolidin-3-yl)thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-methylcarbapen-2-em-3-carboxylate

HRID 568227Notes

Reaction equation

HRID 568227 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[C@H:11]([CH2:12][OH:13])[CH2:10][C@H:9]([S:14][C:15]2[C@H:16]([CH3:39])[C@@H:17]3[C@@H:27]([C@H:28]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH3:29])[C:26](=[O:38])[N:18]3[C:19]=2[C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])[CH2:8]1)=[O:6])[CH:2]=[CH2:3].C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([NH3+])CC.C([NH3+])CC.C([NH3+])CC.C([NH3+])CC.[Ru]([O-])(=O)(=O)=O.[Ru]([O-])(=O)(=O)=O.[Ru]([O-])(=O)(=O)=O>[CH2:1]([O:4][C:5]([N:7]1[C@H:11]([CH:12]=[O:13])[CH2:10][C@H:9]([S:14][C:15]2[C@H:16]([CH3:39])[C@@H:17]3[C@@H:27]([C@H:28]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:32])[CH3:33])[CH3:29])[C:26](=[O:38])[N:18]3[C:19]=2[C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])[CH2:8]1)=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 131722312HCID 131722312, compound

Product 1

HCID 131722311allyl(1R,5S,6S)-2-((3S,5S)-1-allyloxycarbonyl-5-formylpyrrolidin-3-yl)thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-methylcarbapen-2-em-3-carboxylateYield 82.8%

Reagents, catalysts & solvents 2

HCID 178458035HCID 178458035, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Tetrakis(n-propylammonium) perruthenate (VII) (45 mg) is added a solution of 871 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(hydroxymethyl)pyrrolidin-3-yl]thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-methylcarbapen-2-em-3-carboxylate, 272 mg of N-methylmorpholine N-oxide, and 750 mg of 4A active molecular sieves (powder) in 3 ml of dry dichloromethane, and the mixture is stirred in an argon atmosphere at room temperature for 10 min. The reaction solution as such is purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1) to give 719 mg of allyl(1R,5S,6S)-2-((3S,5S)-1-allyloxycarbonyl-5-formylpyrrolidin-3-yl)thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-methylcarbapen-2-em-3-carboxylate as a colorless viscous material.

Workup

  1. customThe reaction solution as such is purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-b47ceed8271d45ec880d65167504b533
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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