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

HRID 2423471Notes

Reaction equation

HRID 2423471 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-28b310487f6b45dcb6801f76ae638c98
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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