m-Chloroperbenzoic acid → N-[(4-chlorophenyl)methyl]-1-(3-methylsulfinylpropyl)-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

HRID 1068007노트

반응식

HRID 1068007 반응식
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:17]=3)[N:12]([CH2:28][CH2:29][CH2:30][S:31][CH3:32])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=[O:43])=CC=1.ClC1C=C(C=CC=1)C(OO)=O>ClCCl>[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:17]=3)[N:12]([CH2:28][CH2:29][CH2:30][S:31]([CH3:32])=[O:43])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 521998p-Toluenesulfonic acid monohydrateHCID 16073877N-[(4-chlorophenyl)methyl]-1-(3-methylsulfanylpropyl)-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

생성물 1

HCID 16073880N-[(4-chlorophenyl)methyl]-1-(3-methylsulfinylpropyl)-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide수율 67.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of N-(4-chlorobenzyl)-1-[3-(methylsulfanyl)propyl]-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxamide (0.10 gm) from Example No. 61 in dichloromethane (2 mL) at 0° C. is added p-toluenesulfonic acid hydrate (0.04 gm) followed by m-chloroperoxybenzoic acid (˜85%)(0.045 gm). The mixture is stirred for 0.5 hrs. The reaction mixture is diluted with dichloromethane, washed with saturated aqueous sodium sulfite, saturated aqueous sodium bicarbonate, brine, dried (Na2SO4) and concentrated under reduced pressure. The crude product is purified by flash column chromatography eluting with 3% to 9% methanol in dichloromethane. The product fractions are combined and recrystallized from ethyl acetate-methanol-hexanes to afford 0.07 gm of the title compound as a white solid.

후처리

  1. washwashed with saturated aqueous sodium sulfite, saturated aqueous sodium bicarbonate, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product is purified by flash column chromatography
  5. washeluting with 3% to 9% methanol in dichloromethane
  6. customrecrystallized from ethyl acetate-methanol-hexanes

출처 및 근거

ORD 기록
ord-cfb64910d6fb443ba511e62990da20cc
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248739B1

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