Trifluoroacetic acid → 3,5-Dichloro-N-(3-chloro-5-((isobutylamino)methyl)benzyl)-2-hydroxy-N-isobutylbenzenesulfonamide

HRID 1889641노트

반응식

HRID 1889641 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([CH2:21][N:22]([CH2:35][CH:36]([CH3:38])[CH3:37])[S:23]([C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[C:27]=2[OH:34])(=[O:25])=[O:24])[CH:20]=1)[CH2:5][N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:33][C:28]1[C:27]([OH:34])=[C:26]([S:23]([N:22]([CH2:21][C:19]2[CH:18]=[C:4]([CH2:5][NH:6][CH2:14][CH:15]([CH3:17])[CH3:16])[CH:3]=[C:2]([Cl:1])[CH:20]=2)[CH2:35][CH:36]([CH3:37])[CH3:38])(=[O:25])=[O:24])[CH:31]=[C:30]([Cl:32])[CH:29]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 58531453tert-butyl 3-chloro-5-((3,5-dichloro-2-hydroxy-N-isobutylphenylsulfonamido)methyl)benzyl(isobutyl)carbamate

생성물 1

HCID 585315243,5-Dichloro-N-(3-chloro-5-((isobutylamino)methyl)benzyl)-2-hydroxy-N-isobutylbenzenesulfonamide수율 93.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl 3-chloro-5-((3,5-dichloro-2-hydroxy-N-isobutylphenylsulfonamido)methyl)benzyl(isobutyl)carbamate (0.23 g, 0.38 mmol) in methylene chloride (5 mL) was added TFA (0.87 mL, 11.3 mmol). The reaction mixture was stirred at rt for 2 h., concentrated and the residue was partitioned between saturated NaHCO3 solution and ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated to give the desired product as white solid (0.18 g, 92%). 1H NMR (CD3OD): δ 7.45 (d, J=2.8 Hz, 2H), 7.40 (s, 2H), 7.37 (s, 1H), 7.31 (d, J=2.8 Hz, 1H), 4.57 (s, 2H), 4.07 (s, 2H), 3.04 (d, J=7.2 Hz, 2H), 2.80 (d, J=7.2 Hz, 2H), 2.00 (m, 1H), 1.68 (m, 1H), 1.00 (d, J=6.6 Hz, 6H), 0.76 (d, J=6.6 Hz, 6H); MS (ESI): (M+H)+=507.22, 509.21.

후처리

  1. concentrationconcentrated
  2. customthe residue was partitioned between saturated NaHCO3 solution and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f139fadde65949fdbb90665035f403d9
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501992B2

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