Sodium Sulfite → HCID 66778076, compound

HRID 2091339Notes

Reaction equation

HRID 2091339 reaction equation
[CH:1]1([CH:7]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([NH:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[O:32])=[CH:27][CH:26]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21]SC)=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:42]1C=CC=C(C(OO)=O)C=1.[S:52]([O-:55])([O-])=[O:53].[Na+].[Na+]>CC(C)=O>[CH:1]1([CH:7]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([NH:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[O:32])=[CH:27][CH:26]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][S:52]([CH3:42])(=[O:55])=[O:53])=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 66777093HCID 66777093, compound

Product 1

HCID 66778076HCID 66778076, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 3-[({4-[(cyclohexyl{3-methyl-5-[3-(methylsulfanyl)propoxy]-1-benzofuran-2-yl}methyl)amino]phenyl}carbonyl)amino]propanoate (0.16 g) synthesized in Example A151(1) was dissolved in acetone (5 mL), metachloroperbenzoic acid (0.2 g) was added to the solution under ice-cooling, and the mixture was stirred for 15 min. To the reaction mixture was added sodium sulfite aqueous solution, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1, volume ratio) to give the title object compound (0.11 g, 68%) as a yellow oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. concentrationThe extract was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1, volume ratio)

Sources & evidence

ORD record
ord-30accec0812548c083c29b3f8195df6e
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

Loading…