Dimethylacetamide → allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethoxymethyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 1464737Notes

Reaction equation

HRID 1464737 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[C@@H:6]([CH3:21])[C:7]([S:18]([CH3:20])=O)=[C:8]2[C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])[CH3:3].[CH2:22]([O:25][C:26]([N:28]1[CH2:32][C@@H](S)[CH2:30][C@H:29]1[CH2:34][O:35][CH2:36][CH2:37][F:38])=[O:27])[CH:23]=[CH2:24].CC(N(C)C)=O>CN(C)C=O>[CH2:22]([O:25][C:26]([N:28]1[CH2:32][C@@H:20]([S:18][C:7]2[C@H:6]([CH3:21])[C@H:5]3[N:9]([C:10](=[O:11])[C@@H:4]3[C@H:2]([OH:1])[CH3:3])[C:8]=2[C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])[CH2:30][C@H:29]1[CH2:34][O:35][CH2:36][CH2:37][F:38])=[O:27])[CH:23]=[CH2:24]

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 57058048allyl (4R,5S,6S)-6-((1R)-1-hydroxyethyl)-4-methyl-3-methylsulfinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateHCID 57241269HCID 57241269, compound

Product 1

HCID 57017483allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethoxymethyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateYield 65.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of allyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-methylsulfinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (150 mg) and silica gel (300 mg) in N,N-dimethylformamide (1.5 ml) was added a solution of (2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethoxymethyl)-4-mercaptopyrrolidine (150 mg) i dimethylacetamide (1.45 g). The mixture was stirred for 2 hours at ambient temperature. Silica gel was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography to afford allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethoxymethyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (160 mg).

Workup

  1. customSilica gel was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-c29fcdbfd70d4068a14cacf540be8b61
Source dataset
uspto-grants-1994_04
Patent number
US05306816

Reaction notes

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