Water → HCID 10047761, compound

HRID 1352716Notes

Reaction equation

HRID 1352716 reaction equation
O.[CH2:2]([C:4]1[C:8]([O:9][C:10]2[CH:11]=[C:12]([C:18]#[N:19])[CH:13]=[C:14]([CH:17]=2)[C:15]#[N:16])=[C:7]([CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([S:29][CH3:30])=[CH:25][CH:24]=2)[NH:6][N:5]=1)[CH3:3].[OH:31]OS([O-])=O.[K+]>ClCCl>[CH2:2]([C:4]1[C:8]([O:9][C:10]2[CH:11]=[C:12]([C:18]#[N:19])[CH:13]=[C:14]([CH:17]=2)[C:15]#[N:16])=[C:7]([CH2:20][CH2:21][O:22][C:23]2[CH:24]=[CH:25][C:26]([S:29]([CH3:30])=[O:31])=[CH:27][CH:28]=2)[NH:6][N:5]=1)[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 9844154HCID 9844154, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 10047761HCID 10047761, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Wet alumina was prepared by adding water (1 ml) to Brockman grade I alumina (5 g). A sample of this material (160 mg) was added to a stirred solution of the sulfide from Example 1 (106 mg, 0.16 mmol) in dichloromethane (1 ml), followed by oxone (98 mg, 0.16 mmol). The reaction mixture was heated at reflux for 45 minutes, before being filtered. The solids were washed with dichloromethane (10 ml) and the combined organics were concentrated under reduced pressure. The crude product mixture was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (100:0, 98:2 and 96:4, by volume) to give the title compound as a colourless oil (25 mg).

Workup

  1. customWet alumina was prepared
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 45 minutes
  4. filtrationbefore being filtered
  5. washThe solids were washed with dichloromethane (10 ml)
  6. concentrationthe combined organics were concentrated under reduced pressure
  7. customThe crude product mixture was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (100:0, 98:2 and 96:4, by volume)

Sources & evidence

ORD record
ord-db1677d114cc47f5bbff5b3cd1d182ea
Source dataset
uspto-grants-2007_05
Patent number
US07220772B2

Reaction notes

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