Methanol → HCID 68514207, compound

HRID 1877172Notes

Reaction equation

HRID 1877172 reaction equation
[CH:1]1([CH:7]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([NH:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:30])=[CH:25][CH:24]=2)[C:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10][C:9]=2[CH2:19]SC)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O[O:40][S:41]([O-:43])=O.[K+].[CH3:45]O>O>[CH:1]1([CH:7]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]([NH:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:30])=[CH:27][CH:28]=2)[C:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10][C:9]=2[CH2:19][S:41]([CH3:45])(=[O:43])=[O:40])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 68515499HCID 68515499, compound

Product 1

HCID 68514207HCID 68514207, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Ethyl 3-[({4-[(cyclohexyl{2-[(methylsulfanyl)methyl]-5-phenylfuran-3-yl}methyl)amino]phenyl}carbonyl)amino]propanoate (267 mg) was dissolved in methanol (9 mL) and water (1 mL), OXONE (0.6 g) was added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (10% ethyl acetate/hexane to 75% ethyl acetate/hexane) to give the title compound (229 mg, 81%) as an amorphous compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (10% ethyl acetate/hexane to 75% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-daf258ab67de404c9458b6b969db34fa
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

Loading…