m-Chloroperbenzoic acid → Ethyl 6-[4-({[3-{[(2,6-dichlorophenyl)sulfinyl]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate

HRID 2423471노트

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HRID 2423471 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9][CH2:10][C:11]1[C:15]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]=[C:29]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:28]=[CH:27]4)=[CH:20][CH:19]=2)=[C:14]([CH:39]([CH3:41])[CH3:40])[O:13][N:12]=1.ClC1C=C(C=CC=1)C(OO)=[O:47].C(=O)(O)[O-].[Na+]>ClCCl>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[S:9]([CH2:10][C:11]1[C:15]([CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]=[C:29]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:28]=[CH:27]4)=[CH:22][CH:23]=2)=[C:14]([CH:39]([CH3:40])[CH3:41])[O:13][N:12]=1)=[O:47]

참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 59321572Ethyl 6-[4-({[3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate

생성물 1

HCID 59321539Ethyl 6-[4-({[3-{[(2,6-dichlorophenyl)sulfinyl]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate수율 57.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of ethyl 6-[4-({[3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (20 mg, 0.033 mmol) in dichloromethane (1 mL) at 0° C. was added meta-chloroperoxybenzoic acid (15 mg, 0.066 mmol). The mixture was stirred at 0° C. for approximately 30 minutes. Aqueous sodium bicarbonate was added and the mixture was extracted twice with dichloromethane. The combined organic layers were dried over magnesium sulfate, adsorbed onto silica gel and purified by chromatography (silica gel, 0-100% ethyl acetate in hexanes gradient elution) to afford ethyl 6-[4-({[3-{[(2,6-dichlorophenyl)sulfinyl]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (12 mg, 0.019 mmol, 57%). 1H-NMR (400 MHz, CDCl3) δ 8.39 (d, J=9 Hz, 1H), 8.23 (d, J=9 Hz, 2H), 8.05-8.03 (m, 2H), 7.68 (d, J=9 Hz, 2H), 7.31 (s, 3H), 7.07 (d, J=9 Hz, 2H), 5.10-4.90 (m, 2H), 4.80-4.58 (m, 2H), 3.22 (septet, J=7 Hz, 1H), 1.32 (d, J=7 Hz, 6H). LRMS m/z 623 (M+H)+.

후처리

  1. extractionthe mixture was extracted twice with dichloromethane
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. custompurified by chromatography (silica gel, 0-100% ethyl acetate in hexanes gradient elution)

출처 및 근거

ORD 기록
ord-28b310487f6b45dcb6801f76ae638c98
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960552B2

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