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

HRID 989501ノート

反応式

HRID 989501 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

(+,−) 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.

後処理

  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

出典と根拠

ORDレコード
ord-94f8fd78886a43c5aa1d89af3baa434c
出典データセット
uspto-grants-2003_10
特許番号
US06639107B1

反応ノート

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