N-(4-(4-methoxybenzyloxy)-3-(3-trifluoromethylphenyl)benzyl)-4-fluoro-N-methylbenzenesulfonamide → N-(3-(3-trifluoromethylphenyl)-4-hydroxybenzyl)-4-fluoro-N-methylbenzenesulfonamide

HRID 68618

반응식

HRID 68618 반응식
COC1C=CC(C[O:8][C:9]2[CH:27]=[CH:26][C:12]([CH2:13][N:14]([CH3:25])[S:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:11][C:10]=2[C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)=CC=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:37][C:34]([F:35])([F:36])[C:30]1[CH:29]=[C:28]([C:10]2[CH:11]=[C:12]([CH:26]=[CH:27][C:9]=2[OH:8])[CH2:13][N:14]([CH3:25])[S:15]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:33]=[CH:32][CH:31]=1

참가 물질

3

반응물 1

HCID 66868532N-(4-(4-methoxybenzyloxy)-3-(3-trifluoromethylphenyl)benzyl)-4-fluoro-N-methylbenzenesulfonamide

생성물 1

HCID 66868277N-(3-(3-trifluoromethylphenyl)-4-hydroxybenzyl)-4-fluoro-N-methylbenzenesulfonamide수율 64%

시약·촉매·용매 1

HCID 21863450Trifluoroacetic acid methylene chloride용매

실험 절차

Intermediate 35 (700 mg, 1.25 mmol) was dissolved in TFA/DCM (1/1) and stirred at room temperature for 1 h. Solvent was removed in vacuo and the residue was purified via silica gel chromatography (0-40% EtOAc/hexane) to afford 350 mg (64%) of N-(3-(3-trifluoromethylphenyl)-4-hydroxybenzyl)-4-fluoro-N-methylbenzenesulfonamide (36). 1HNMR (CD3OD, 400 MHz): δ 7.91 (m, 2H), 7.80 (s, 1H), 7.65 (m, 2H), 7.59 (d, 1H), 7.15-7.25 (m, 4H), 6.94 (d, 1H), 4.97 (s, 1H), 4.13 (s, 2H), 2.64 (s, 3H). MS (ESI): MH+=440.1. HPLC (Method B) tR=3.45 min.

후처리

  1. customSolvent was removed in vacuo
  2. customthe residue was purified via silica gel chromatography (0-40% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-089e0588540140d9bcdba89eff06b05e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822467B2

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