Oxygen → HCID 86664652, compound

HRID 1917388Notes

Reaction equation

HRID 1917388 reaction equation
[C:1]([O:5][C:6]([C@@:8]1([CH2:31][CH:32]=C)[C@@H:12]([CH2:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11](=[O:22])[N:10]([C@@H:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH3:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:34]=O.CSC>CO>[C:1]([O:5][C:6]([C@@:8]1([CH2:31][CH:32]=[O:34])[C@@H:12]([CH2:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11](=[O:22])[N:10]([C@@H:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH3:24])[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 977OxygenHCID 1068Dimethyl SulfideHCID 67490769HCID 67490769, compound

Product 1

HCID 86664652HCID 86664652, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3S,4S)-3-allyl-4-benzyloxymethyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (6.76 g, 15.0 mmol) in methanol (150 mL) was bubbled with oxygen for five minutes. After bubbling with ozone for 1.5 hours with stirring under cooling with dry ice-methanol, ozone was removed by bubbling with nitrogen. Dimethyl sulfide (5.64 mL, 76.8 mmol) was added under cooling, and the mixture was stirred for 19 hours. The reaction solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→90:10→80:20→75:25→66:34→50:50) to give 4.58 g of the title compound as a transparent oil.

Workup

  1. customAfter bubbling with ozone for 1.5 hours
  2. temperatureunder cooling with dry ice-methanol, ozone
  3. customwas removed
  4. customby bubbling with nitrogen
  5. temperatureunder cooling
  6. stirringthe mixture was stirred for 19 hours
  7. concentrationThe reaction solution was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→90:10→80:20→75:25→66:34→50:50)

Sources & evidence

ORD record
ord-0d3225d4e1624f8dbc46a8bd40c67b66
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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