2-Methoxypropene → HCID 15276490, compound

HRID 1489453Notes

Reaction equation

HRID 1489453 reaction equation
CO[C:3]([CH3:5])=[CH2:4].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1[C@H:31]([NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@@H:32]([OH:37])[C:33]([O:35][CH3:36])=[O:34]>C1C=CC=CC=1>[C:42]([O:41][C:39]([N:38]1[C@@H:31]([C:25]2[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:24]=2[F:23])[C@H:32]([C:33]([O:35][CH3:36])=[O:34])[O:37][C:3]1([CH3:5])[CH3:4])=[O:40])([CH3:45])([CH3:44])[CH3:43]

Participants

5

Reactant 3

HCID 83002-Methoxypropene3×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 15276486HCID 15276486, compound

Product 1

HCID 15276490HCID 15276490, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.3 ml of isopropenyl methyl ether and 39 mg of pyridinium p-toluenesulfonate were added to a solution of 515 mg of methyl (2R,3S)-3-(2,4-difluorophenyl)-3-tert-butoxycarbonylamino-2-hydroxypropionate dissolved in 30 ml of benzene, and the mixture was stirred at room temperature for 30 minutes. The mixture was further stirred at 90° C. for 30 minutes and then returned to room temperature. 0.3 ml of isopropenyl methyl ether was added to the mixture, and the resulting mixture was stirred at 90° C. for 30 minutes. The mixture was cooled again to room temperature, 0.15 ml of isopropenyl methyl ether was added thereto, and the mixture was stirred at 90° C. for 4 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (solvent; toluene:ethyl acetate=50:1) to obtain 428 mg of methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(2,4-difluorophenyl)-5-oxazolidinecarboxylate.

Workup

  1. stirringThe mixture was further stirred at 90° C. for 30 minutes
  2. customreturned to room temperature
  3. stirringthe resulting mixture was stirred at 90° C. for 30 minutes
  4. temperatureThe mixture was cooled again to room temperature
  5. stirringthe mixture was stirred at 90° C. for 4 hours
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (solvent; toluene:ethyl acetate=50:1)

Sources & evidence

ORD record
ord-0e8079f8b89f4514bddb4cdf5e117f9a
Source dataset
uspto-grants-1997_10
Patent number
US05677470

Reaction notes

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