Hydrogen Peroxide → HCID 67224897, 화합물

HRID 1944764

반응식

HRID 1944764 반응식
[OH-:1].[Na+].OO.[C:5]([C:7]1([NH:27][C:28](=O)[CH3:29])[CH2:12][CH2:11][CH:10]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH3:25])=[C:19]([CH3:26])[CH:18]=2)(=[O:16])=[O:15])[CH2:9][CH2:8]1)#[N:6]>C(O)C.O>[CH2:24]([O:23][C:20]1[CH:21]=[CH:22][C:17]([S:14]([NH:13][CH:10]2[CH2:9][CH2:8][C:7]3([N:27]=[C:28]([CH3:29])[NH:6][C:5]3=[O:1])[CH2:12][CH2:11]2)(=[O:15])=[O:16])=[CH:18][C:19]=1[CH3:26])[CH3:25]

참가 물질

6

반응물 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 67223797N-(1-cyano-4-(4-ethoxy-3-methylphenylsulfonamido)cyclohexyl)acetamide2회

생성물 1

HCID 67224897HCID 67224897, 화합물수율 48.3%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

5N Sodium hydroxide (320 ul, 1.59 mmol) followed by 50% aqueous hydrogen peroxide (157 ul, 2.55 mmol) were added to solution of N-(1-cyano-4-(4-ethoxy-3-methylphenylsulfonamido)cyclohexyl)acetamide (Intermediate 126, 242 mg, 0.638 mmol) in ethanol (6.4 ml). The reaction was heated to 80° C. for three hours. LCMS indicated approximately 3:1 product:starting material by co-injection. The reaction was diluted with water and extract with four volumes ethyl acetate. The combined organics were dried over sodium sulfate, filtered and concentrate to 226 mg crude. TLC (10% methanol in ethyl acetate): Rf starting material 0.66; major spot Rf=0.25. The crude was chromatographed on Biotage 12M eluting 0-100% ethyl acetate in (10% methanol in ethyl acetate) to give the product as an off-white solid (117 mg, 0.308 mmol). LCMS [M+H]=380.2.

후처리

  1. extractionextract with four volumes ethyl acetate
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrate to 226 mg crude
  5. customThe crude was chromatographed on Biotage 12M
  6. washeluting 0-100% ethyl acetate in (10% methanol in ethyl acetate)

출처 및 근거

ORD 기록
ord-1e07e2d0db0a4902aa10cc40ff7066e6
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394858B2

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