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

HRID 1889641ノート

反応式

HRID 1889641 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f139fadde65949fdbb90665035f403d9
出典データセット
uspto-grants-2013_08
特許番号
US08501992B2

反応ノート

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