Acetyl chloride → N-(1-cyano-4-(4-ethoxy-3-methylphenylsulfonamido)cyclohexyl)acetamide

HRID 1944742

반응식

HRID 1944742 반응식
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1([C:26]#[N:27])[CH2:11][CH2:10][CH:9]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[C:18]([CH3:25])[CH:17]=2)(=[O:15])=[O:14])[CH2:8][CH2:7]1.C(OCC)(=O)C>ClCCl.CCCCCCC>[C:26]([C:6]1([NH:5][C:1](=[O:3])[CH3:2])[CH2:7][CH2:8][CH:9]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[C:18]([CH3:25])[CH:17]=2)(=[O:14])=[O:15])[CH2:10][CH2:11]1)#[N:27]

참가 물질

6

반응물 3

HCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 67224098HCID 67224098, 화합물2회

생성물 1

HCID 67223797N-(1-cyano-4-(4-ethoxy-3-methylphenylsulfonamido)cyclohexyl)acetamide수율 77.7%

시약·촉매·용매 2

HCID 6344Dichloromethane용매3회HCID 8900Heptane용매

실험 절차

Acetyl chloride (0.106 g, 1.356 mmol) in dichloromethane (1 ml) was added to room temperature solution of N-(4-amino-4-cyanocyclohexyl)-4-ethoxy-3-methylbenzenesulfonamide (Intermediate 124, 0.366 g, 1.085 mmol) in dichloromethane (9 ml) and the reaction was stirred 18 hours. The reaction was diluted with dichloromethane and rinsed with two volumes of saturated sodium bicarbonate. The organics were dried over magnesium sulfate, filtered, and concentrated to yield 464 mg of a crude film. TLC (50% ethyl acetate in heptane) indicated a major spot Rf=0.07 by UV. The crude product was chromatographed on Biotage 25S by TLC generated gradient to yield N-(1-cyano-4-(4-ethoxy-3-methylphenylsulfonamido)cyclohexyl)-acetamide (320 mg, 0.843 mmol) as a colorless solid. Carbon-13 NMR displayed a characteristic signature for nitrile at 119.1 ppm along with a signal at 110.7 ppm for the aromatic carbon ortho to aryl ether; in addition the peaks at 169.7 ppm and 160.97 ppm represent the amide and ipso-carbon of the aryl ether (no assignment implied). LCMS [M+H]=380.2.

후처리

  1. washrinsed with two volumes of saturated sodium bicarbonate
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield 464 mg of a crude film
  6. customThe crude product was chromatographed on Biotage 25S by TLC

출처 및 근거

ORD 기록
ord-e5d23d4e28784654ac9828b58249dabd
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394858B2

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