HCID 45256133, compound → HCID 56602957, compound

HRID 386909Notes

Reaction equation

HRID 386909 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[OH:14][CH2:15][C:16]([C:19]1[CH:23]=[C:22]([NH:24][C:25](=[O:38])[C:26]([CH3:37])([S:28]([CH:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)(=[O:30])=[O:29])[CH3:27])[O:21][N:20]=1)([CH3:18])[CH3:17]>CC(C)=O.ClCCl>[CH3:17][C:16]([C:19]1[CH:23]=[C:22]([NH:24][C:25](=[O:38])[C:26]([CH3:37])([S:28]([CH:31]2[CH2:32][CH2:33][O:34][CH2:35][CH2:36]2)(=[O:30])=[O:29])[CH3:27])[O:21][N:20]=1)([CH3:18])[C:15]([OH:3])=[O:14]

Participants

5

Reactant 2

HCID 45256133HCID 45256133, compoundHCID 131709961Jones' reagent

Product 1

HCID 56602957HCID 56602957, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Jones reagent (1.28 mL, 10.24 mmol) is added dropwise to a solution of N-[3-(2-Hydroxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionamide (560 mg, 1.50 mmol) in a mixture of acetone (4 mL) and dichloromethane (4 mL) at 0° C. The reaction mixture is stirred at 0° C. for 3 minutes then room temperature for 2.5 h. After this time, the reaction mixture is diluted with acetone and filtered through celite and the celite is washed with acetone. The filtrate is concentrated under reduced pressure. The residue is dispersed in water and filtered to yield the title compound. Yield: 64%; m/z 389 [M+H].

Workup

  1. waitroom temperature for 2.5 h
  2. filtrationfiltered through celite
  3. washthe celite is washed with acetone
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. additionThe residue is dispersed in water
  6. filtrationfiltered

Sources & evidence

ORD record
ord-ec3576c714f943b1bc0d040a4f750206
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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