Ethanesulfonyl chloride → Methyl (4-{[{4-[(4-butylphenyl)ethynyl]benzyl}(ethylsulfonyl)-amino]methyl}phenoxy)acetate

HRID 551915

반응식

HRID 551915 반응식
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:33]=[CH:32][C:16]([CH2:17][NH:18][CH2:19][C:20]3[CH:31]=[CH:30][C:23]([O:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH2:34]([S:36](Cl)(=[O:38])=[O:37])[CH3:35]>N1C=CC=CC=1.Cl>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:17][N:18]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([O:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:30][CH:31]=3)[S:36]([CH2:34][CH3:35])(=[O:38])=[O:37])=[CH:32][CH:33]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

5

반응물 2

HCID 11667Ethanesulfonyl chlorideHCID 57554567Methyl {4-[({4-[(4-butylphenyl)ethynyl]benzyl}amino)methyl]phenoxy}acetate

생성물 1

HCID 11555583Methyl (4-{[{4-[(4-butylphenyl)ethynyl]benzyl}(ethylsulfonyl)-amino]methyl}phenoxy)acetate수율 15.3%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 1049Pyridine용매

반응 조건

온도
0 °C

실험 절차

To a cold solution (0° C.) of methyl {4-[({4-[(4-butylphenyl)ethynyl]benzyl}amino)-methyl]phenoxy}acetate (38 mg, 0.086 mmol) in anhydrous pyridine (2 mL) was added ethanesulfonyl chloride (Fluka, 40 ∞l, 0.43 mmol) and the reaction mixture was stirred at 0° C. for 4 hrs and at rt for an additional 15 hours. The reaction mixture was diluted with an aqueous solution of HCl (1N) and extracted with DCM (3×). The combined organic layers were dried over MgSO4 and the solvent was removed under reduced pressure. Purification by flash chromatography on silicagel (cHex/EtOAc) gave 7 mg (15%) of the title compound as a colorless oil. LC/MS, M+(ESI): 534.3 (purity: 94.5%).

후처리

  1. extractionextracted with DCM (3×)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. customthe solvent was removed under reduced pressure
  4. customPurification by flash chromatography on silicagel (cHex/EtOAc)

출처 및 근거

ORD 기록
ord-5f15bf8530b94124adec123fba881f2f
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947851B2

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