Benzoyl chloride → (+,-) Cis N-{4-[2-(Propane-2-sulfonylamino)-cyclopentyl]-phenyl}-benzamide

HRID 989501노트

반응식

HRID 989501 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:4][CH:3]=1.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[CH3:18][CH:17]([S:14]([NH:13][C@H:9]1[CH2:10][CH2:11][CH2:12][C@H:8]1[C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:7][CH:6]=1)(=[O:16])=[O:15])[CH3:19]

참가 물질

4

반응물 2

HCID 7412Benzoyl chlorideHCID 59103295cis-[2-(4-Aminophenyl)cyclopentyl][(methylethyl)sulfonyl]amine

생성물 1

HCID 69112909(+,-) Cis N-{4-[2-(Propane-2-sulfonylamino)-cyclopentyl]-phenyl}-benzamide수율 33%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

(+,−) Cis propane-2-sulfonic acid [2-(4-amino-phenyl)-cyclopentyl]-amide (265 mg, 0.94 mmol, prepared in example 23) was dissolved in 10 mL of methylene chloride and cooled to 0° C. under nitrogen. Benzoyl chloride was added (120 uL, 1.03 mmol) and after stirring 15 min the ice bath was removed and stirring continued for 2 hours. The reaction was diluted with methylene chloride and washed with water, then 0.1 N HCl and dried over sodium sulfate. The organic phase was concentrated in vacuo to 360 mg crude oil. The product was purified by radial chromatography eluting first with 70:30 methylene chloride:hexanes then ethyl acetate was added (→20%) until all bands were removed to give 120 mg (33%) of the title compound as a white solid. The NMR was consistent with the assigned structure.

후처리

  1. customwas removed
  2. additionThe reaction was diluted with methylene chloride
  3. washwashed with water
  4. dry with material0.1 N HCl and dried over sodium sulfate
  5. concentrationThe organic phase was concentrated in vacuo to 360 mg crude oil
  6. customThe product was purified by radial chromatography
  7. washeluting first with 70:30 methylene chloride
  8. additionhexanes then ethyl acetate was added (→20%) until all bands
  9. customwere removed

출처 및 근거

ORD 기록
ord-94f8fd78886a43c5aa1d89af3baa434c
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06639107B1

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