Methanol → HCID 10320825, compound

HRID 1352717Notes

Reaction equation

HRID 1352717 reaction equation
[CH2:1]([C:3]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([C:17]#[N:18])[CH:12]=[C:13]([CH:16]=2)[C:14]#[N:15])=[C:6]([CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25](SC)=[CH:24][CH:23]=2)[NH:5][N:4]=1)[CH3:2].O[O:31][S:32]([O-:34])=O.[K+].[CH3:36]O>O>[CH2:1]([C:3]1[C:7]([O:8][C:9]2[CH:16]=[C:13]([C:14]#[N:15])[CH:12]=[C:11]([CH:10]=2)[C:17]#[N:18])=[C:6]([CH2:19][CH2:20][O:21][C:22]2[CH:23]=[CH:24][C:25]([S:32]([CH3:36])(=[O:34])=[O:31])=[CH:26][CH:27]=2)[NH:5][N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 9844154HCID 9844154, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 10320825HCID 10320825, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of the sulfide from Example 1 (90 mg, 0.22 mmol) in methanol (2 ml) at 0° C. was added a solution of oxone (205 mg, 0.33 mmol) in water (2 ml). The viscous suspension was further diluted with methanol (2 ml). After 4 hours the reaction mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (20 ml) and water (20 ml). The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product mixture was purified by flash chromatography on silica gel eluting with pentane:ethyl acetate (50:50, by volume) to give the title compound (70 mg) as a white powder, m.p. 88–90° C.

Workup

  1. concentrationAfter 4 hours the reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between dichloromethane (20 ml) and water (20 ml)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product mixture was purified by flash chromatography on silica gel eluting with pentane:ethyl acetate (50:50, by volume)

Sources & evidence

ORD record
ord-bf365ce7fa054c46ab0581a9078bd254
Source dataset
uspto-grants-2007_05
Patent number
US07220772B2

Reaction notes

Loading…