Dimethyl Sulfoxide → 4-(Aminocarbonyl)-3-(cyclobutyloxy)benzoic acid

HRID 906106노트

반응식

HRID 906106 반응식
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][C:4]=1[O:13][CH:14]1[CH2:17][CH2:16][CH2:15]1)#[N:2].CS(C)=[O:20].[OH-].[Na+].OO>C(O)C.O>[NH2:2][C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[O:13][CH:14]1[CH2:17][CH2:16][CH2:15]1)=[O:20]

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 67404284Methyl 4-cyano-3-(cyclobutyloxy)benzoate

생성물 1

HCID 577484714-(Aminocarbonyl)-3-(cyclobutyloxy)benzoic acid수율 50%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a solution of methyl 4-cyano-3-(cyclobutyloxy)benzoate (0.051 g, 0.23 mmol) in 2 ml of ethanol was added 0.5 ml of DMSO, 1 ml of 1N aqueous sodium hydroxide, 1 ml of 30% aqueous hydrogen peroxide, and the reaction mixture was stirred at RT for 18 hrs. The reaction mixture was diluted with 10 ml of water and the aqueous solution extracted three times with ethyl acetate (20 ml). The aqueous layer was acidified to pH 3-4 by portion-wise addition of aqueous hydrochloric acid, then extracted with ethyl acetate (3×20 mL). The organic solution was rotary evaporated to dryness and dried in vacuo to provide 4-(aminocarbonyl)-3-(cyclobutyloxy)benzoic acid (0.026 g, 50%). 1H NMR (400 MHz, DMSO-d6): 13.25 (s, 1H), 7.80 (d, 1H), 7.68 (s, 1H), 7.63 (s, 1H), 7.55 (d, 1H), 7.41 (s, 1H), 4.88-4.85 (m, 1H), 2.44-2.43 (m, 2H), 2.18-2.14 (m, 2H), 1.99-1.73 (m, 2H). MS (EI) for C12H13NO4: 236 (MH+).

후처리

  1. extractionthe aqueous solution extracted three times with ethyl acetate (20 ml)
  2. additionThe aqueous layer was acidified to pH 3-4 by portion-wise addition of aqueous hydrochloric acid
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. customThe organic solution was rotary evaporated to dryness
  5. customdried in vacuo

출처 및 근거

ORD 기록
ord-382adc7161d947ab9eebc225752b4e6e
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012956B2

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