Sodium Chloride → 2-[4-bromo-5-chloro-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenyl]-acetic acid methyl ester

HRID 1891387노트

반응식

HRID 1891387 반응식
[CH3:1][O:2][C:3](=[O:32])[CH:4]([C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([Br:16])=[CH:11][C:10]=1[S:17]([N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH3:31])([CH3:30])[CH2:22][CH2:21]1)(=[O:19])=[O:18])C(OC)=O.[Na+].[Cl-]>CS(C)=O.O>[CH3:1][O:2][C:3](=[O:32])[CH2:4][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([Br:16])=[CH:11][C:10]=1[S:17]([N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH3:30])([CH3:31])[CH2:22][CH2:21]1)(=[O:19])=[O:18]

참가 물질

5

반응물 2

HCID 5234Sodium ChlorideHCID 684691712-[4-bromo-5-chloro-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenyl]-malonic acid dimethyl ester

생성물 1

HCID 684691412-[4-bromo-5-chloro-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenyl]-acetic acid methyl ester수율 79.7%

시약·촉매·용매 2

HCID 962Water촉매HCID 679Dimethyl Sulfoxide용매

실험 절차

2-[4-Bromo-5-chloro-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenyl]-malonic acid dimethyl ester (0.72 g, 1.32 mmol) was heated at 120° C. for 5 hrs in DMSO which contained NaCl (153.5 mg, 2.65 mmol) and 2 drops of water. After cooling to rt, the mixture was extracted with ethyl acetate, washed with water and brine, and was dried over MgSO4. Filtration and concentration yielded a residue which was purified via silica gel flash column chromatography eluting with hexane/ethyl acetate (100/15) to give 2-[4-bromo-5-chloro-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenyl]-acetic acid methyl ester (512 mg). MS: 487.9 (M+H)+; tR=2.75 min (method 1)

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialwas dried over MgSO4
  4. filtrationFiltration and concentration
  5. customyielded a residue which
  6. customwas purified via silica gel flash column chromatography
  7. washeluting with hexane/ethyl acetate (100/15)

출처 및 근거

ORD 기록
ord-abd6f065437742f38ebc30c091e1a4e0
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507536B2

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