m-Chloroperbenzoic acid → HCID 68536396, compound

HRID 2389342Notes

Reaction equation

HRID 2389342 reaction equation
[C:1]1([CH:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:32])[N:12]([CH2:14][CH2:15][CH2:16][S:17][C:18]3[CH:19]=[C:20]([CH:29]=[CH:30][CH:31]=3)[O:21][CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:44]>C(Cl)Cl>[C:1]1([CH:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:32])[N:12]([CH2:14][CH2:15][CH2:16][S:17]([C:18]3[CH:19]=[C:20]([CH:29]=[CH:30][CH:31]=3)[O:21][CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:44])[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68536298HCID 68536298, compound

Product 1

HCID 68536396HCID 68536396, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-[3-({3-[5-(diphenylmethyl)-2-oxopyridin-1(2H)-yl]propyl}sulfanyl)phenoxy]propanoate (175 mg) in DCM (5 mL) was added 3-chloroperoxybenzoic acid (82 mg) at 0° C. for 20 minutes. The resulting mixture was extracted with EtOAc. The organic layer was washed with saturated NaHCO3 aqueous solution and brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane: EtOAc=1:1-1:10) to afford ethyl 2-[3-({3-[5-(diphenylmethyl)-2-oxopyridin-1(2H)-yl]propyl}sulfinyl)phenoxy]propanoate (170 mg) as a colorless oil.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc
  2. washThe organic layer was washed with saturated NaHCO3 aqueous solution and brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (n-hexane: EtOAc=1:1-1:10)

Sources & evidence

ORD record
ord-7b4854cc53e3448fa0ae98909891bb3e
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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