Water → HCID 21949906, compound

HRID 2114660Notes

Reaction equation

HRID 2114660 reaction equation
O.[CH2:2]([C:4]1[C:8]([O:9][C:10]2[CH:11]=[C:12]([CH:15]=[C:16]([S:18][CH3:19])[CH:17]=2)[C:13]#[N:14])=[C:7]([CH2:20][CH3:21])[N:6]([CH2:22][CH2:23][OH:24])[N:5]=1)[CH3:3].[OH:25]OS([O-])=O.[K+]>ClCCl>[CH2:2]([C:4]1[C:8]([O:9][C:10]2[CH:11]=[C:12]([CH:15]=[C:16]([S:18]([CH3:19])=[O:25])[CH:17]=2)[C:13]#[N:14])=[C:7]([CH2:20][CH3:21])[N:6]([CH2:22][CH2:23][OH:24])[N:5]=1)[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 21949931HCID 21949931, compoundHCID 23707502Potassium hydroxy sulfite2×

Product 1

HCID 21949906HCID 21949906, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Wet alumina was prepared by adding water (1 ml) to Brockman grade I alumina (5 g). To a stirred solution of the sulphide from Example 250 (134 mg, 0.40 mmol) in dichloromethane (2 ml) was added of wet alumina (400 mg) followed by Oxone® (123 mg, 0.4 mmol) and the mixture was heated at reflux. After 1 hour a second portion of oxone (123 mg, 0.40 mmol) was added and the mixture was heated for a further 2 hours. After cooling to room temperature the reaction mixture was filtered and the resulting solids were washed with dichloromethane (20 ml). The filtrate was concentrated and was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (a gradient from 99:1 to 90:10, by volume) to provide the title compound (92 mg) as an oil.

Workup

  1. customWet alumina was prepared
  2. temperaturethe mixture was heated
  3. temperatureat reflux
  4. temperaturethe mixture was heated for a further 2 hours
  5. filtrationwas filtered
  6. washthe resulting solids were washed with dichloromethane (20 ml)
  7. concentrationThe filtrate was concentrated
  8. customwas purified by flash chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-a719f3c7228f464b97d4decd12a004f7
Source dataset
uspto-grants-2008_10
Patent number
US07435728B2

Reaction notes

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