Water → 5-[[1-(4-Chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methoxy-4-methyl-oxazolidin-2-one

HRID 918761Notes

Reaction equation

HRID 918761 reaction equation
[CH3:1][O:2][NH:3][C:4](=O)[O:5]C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C@@H:22]3[C@H:24]([CH3:25])[O:23]3)=[N:16]2)=[CH:11][CH:10]=1.O>CS(C)=O>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]3[O:23][C:4](=[O:5])[N:3]([O:2][CH3:1])[CH:24]3[CH3:25])=[N:16]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12663380methyl N-methoxycarbamateHCID 896501121-(4-chloro-phenyl)-3-[[(2R,3S)-3-methyloxiran-2-yl]methoxy]pyrazole

Product 1

HCID 896501675-[[1-(4-Chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methoxy-4-methyl-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 1.08 g (10.0 mmol) methyl N-methoxycarbamate in 17 ml DMSO have been added with stirring at ambient temperature 1.00 g (8.9 mmol) potassium tert.-butylate. Stirring has been continued for 5 min before 2.00 g (7.56 mmol) 1-(4-chloro-phenyl)-3-[[(2R,3S)-3-methyloxiran-2-yl]methoxy]pyrazole have been added. The mixture was stirred at 90° C. for 20 h. After cooling to ambient temperature the reaction mixture was poured into 150 ml of water, extracted thrice with 30 ml ethyl acetate each, the combined extracts have been dried with sodium sulfate and the solvent removed in vacuo. The crude product (2.5 g) was used without further purification.

Workup

  1. additionhave been added
  2. stirringThe mixture was stirred at 90° C. for 20 h
  3. extractionextracted thrice with 30 ml ethyl acetate each, the combined extracts
  4. dry with materialhave been dried with sodium sulfate
  5. customthe solvent removed in vacuo
  6. customThe crude product (2.5 g) was used without further purification

Sources & evidence

ORD record
ord-6523072674364afe98ed0a6ef5147b03
Source dataset
uspto-grants-2016_03
Patent number
US09271501B2

Reaction notes

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