Water → 5-Oxo-2-phenoxythiocarbonyl-2,5-dihydro-isoxazole-4-carboxylic acid ethyl ester

HRID 2080116Notes

Reaction equation

HRID 2080116 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10](=[O:11])[O:9][NH:8][CH:7]=1)=[O:5])[CH3:2].[CH:12]1[CH:17]=[CH:16][C:15]([O:18][C:19](Cl)=[S:20])=[CH:14][CH:13]=1.N1C=CC=CC=1.O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:10](=[O:11])[O:9][N:8]([C:19]([O:18][C:15]2[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=2)=[S:20])[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 70498Phenyl thioxochloroformateHCID 239539Ethyl 5-Hydroxy-4-isoxazolecarboxylate

Product 1

HCID 105656355-Oxo-2-phenoxythiocarbonyl-2,5-dihydro-isoxazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Oxo-2,5-dihydro-isoxazole-4-carboxylic acid ethyl ester described in Preparation Example 112 (1.00 g, 5.17 mmol), phenyl chlorothionoformate (786 μl, 5.69 mmol) and pyridine (919 μl, 11.4 mmol) were dissolved at 0° C. in toluene (20 mL), and the solution was stirred at room temperature for 17 hours under nitrogen atmosphere. Water was added to the reaction solution at 0° C., which was then extracted with ethyl acetate, and the organic layer was washed with brine. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1), and the title compound (1.66 g, 5.66 mmol, quantitatively) was obtained as a pale yellow solid.

Workup

  1. extractionwhich was then extracted with ethyl acetate
  2. washthe organic layer was washed with brine
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-08918559b62342e291cb36403491f6cf
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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