Sulfuric Acid → 4-(Methylsulfonyl)phenol

HRID 2070231노트

반응식

HRID 2070231 반응식
C1[C:6]([C@H:7]([CH2:12][NH2:13])[CH2:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=C(Cl)C=1.[C:15](=[O:18])([O-:17])[O-].[K+].[K+].[CH3:21][CH:22]([CH3:44])[C:23]([O:25][CH:26](OC([O:33][C:34]1[CH:39]=[CH:38][C:37]([S:40]([CH3:43])(=[O:42])=[O:41])=[CH:36][CH:35]=1)=O)[CH:27](C)C)=[O:24].S(=O)(=O)(O)O.[C:50](#N)C>COC(C)(C)C.O>[CH3:50][CH:5]([CH3:4])[CH2:6][C@H:7]([CH2:12][NH:13][C:15]([O:17][CH2:27][CH2:26][O:25][C:23](=[O:24])[CH:22]([CH3:44])[CH3:21])=[O:18])[CH2:8][C:9]([OH:11])=[O:10].[CH3:43][S:40]([C:37]1[CH:38]=[CH:39][C:34]([OH:33])=[CH:35][CH:36]=1)(=[O:41])=[O:42]

참가 물질

9

반응물 5

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 44602ArbaclofenHCID 592705152-Methyl-1-[4-(methylsulfonyl)phenoxycarbonyloxy]propyl 2-methylpropanoate

생성물 2

HCID 1233504-(Methylsulfonyl)phenolHCID 86640714(3S)-5-Methyl-3-({[(2-methylpropanoyloxy)ethoxy]carbonylamino}methyl)hexanoic Acid

시약·촉매·용매 2

HCID 962Water용매HCID 15413tert-Butyl methyl ether용매

실험 절차

R-Baclofen (2.13 g) and water (50 mL) were charged to a vessel at room temperature. Potassium carbonate (1.6 g) was added in one portion and the mixture was stirred at room temperature for 5 minutes. A solution of 2-methyl-1-[4-(methylsulfonyl)phenoxycarbonyloxy]propyl 2-methylpropanoate D6 (3.5 g) in acetonitrile (50 mL) was added. After 6 hours, tert-butyl methyl ether (50 mL) was added and the reaction mixture was cooled to 5-10° C. A 5% aqueous sulfuric acid was added to adjust the pH to approximately 3. The mixture was then warmed to room temperature and stirred for 10 minutes. The organic layer was washed with water (3×20 mL) and evaporated to provide the crude title compound as an orange oil with 4-(methylsulfonyl)phenol impurity.

후처리

  1. waitAfter 6 hours
  2. temperaturethe reaction mixture was cooled to 5-10° C
  3. temperatureThe mixture was then warmed to room temperature
  4. stirringstirred for 10 minutes
  5. washThe organic layer was washed with water (3×20 mL)
  6. customevaporated

출처 및 근거

ORD 기록
ord-037d556ae9d74d86ab682802c1ce4935
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299291B2

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