Potassium Carbonate → {5-Cyclopropyl-6-[(4-methoxybenzyl)oxy]pyridin-2-yl}[4-(cyclopropylsulfonyl)phenyl]methanol

HRID 70715노트

반응식

HRID 70715 반응식
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([CH:20]([C:22]3[CH:27]=[CH:26][C:25](SC4CC4)=[CH:24][CH:23]=3)[OH:21])=[N:8][C:9]=2[O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:3][CH2:2]1.ClC1C=CC=[C:35]([C:39](OO)=O)[CH:34]=1.[S:43]([O-:47])([O-])(=[O:45])=S.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([CH:20]([C:22]3[CH:23]=[CH:24][C:25]([S:43]([CH:39]4[CH2:35][CH2:34]4)(=[O:47])=[O:45])=[CH:26][CH:27]=3)[OH:21])=[N:8][C:9]=2[O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 67400247{5-Cyclopropyl-6-[(4-methoxybenzyl)oxy]pyridin-2-yl}[4-(cyclopropylsulfanyl)phenyl]methanol

생성물 1

HCID 67400026{5-Cyclopropyl-6-[(4-methoxybenzyl)oxy]pyridin-2-yl}[4-(cyclopropylsulfonyl)phenyl]methanol수율 80%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A solution of {5-cyclopropyl-6-[(4-methoxybenzyl)oxy]pyridin-2-yl}[4-(cyclopropylsulfanyl)phenyl]methanol (469 mg) in chloroform (15 mL) was stirred in an ice bath, and m-chloroperbenzoic acid (560 mg) was added as powder. The mixture was returned to room temperature and stirred for 3.5 hours. The reaction solution was stirred again in an ice bath, and sodium thiosulfate and a potassium carbonate solution were added, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=92:8→34:66) to give {5-cyclopropyl-6-[(4-methoxybenzyl)oxy]pyridin-2-yl}[4-(cyclopropylsulfonyl)phenyl]methanol as a light yellow oil (403 mg, 80%).

후처리

  1. customwas returned to room temperature
  2. stirringThe reaction solution was stirred again in an ice bath
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=92:8→34:66)

출처 및 근거

ORD 기록
ord-7f8a86eb06914d1ca74bff38a97a5f3b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822503B2

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