Triethylamine → tert-butyl 3-chloro-5-((3,5-dichloro-2-hydroxy-N-isobutylphenylsulfonamido)methyl)benzyl(isobutyl)carbamate

HRID 1889640ノート

反応式

HRID 1889640 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([CH2:21][NH:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH:20]=1)[CH2:5][N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].CCN(CC)CC.[Cl:34][C:35]1[C:36]([OH:46])=[C:37]([S:42](Cl)(=[O:44])=[O:43])[CH:38]=[C:39]([Cl:41])[CH:40]=1>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([CH2:21][N:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[S:42]([C:37]2[CH:38]=[C:39]([Cl:41])[CH:40]=[C:35]([Cl:34])[C:36]=2[OH:46])(=[O:43])=[O:44])[CH:20]=1)[CH2:5][N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 66616572Tert-butyl 3-chloro-5-((isobutylamino)methyl)benzyl(isobutyl)carbamate

生成物 1

HCID 58531453tert-butyl 3-chloro-5-((3,5-dichloro-2-hydroxy-N-isobutylphenylsulfonamido)methyl)benzyl(isobutyl)carbamate収率 73.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of tert-butyl 3-chloro-5-((isobutylamino)methyl)benzyl(isobutyl)carbamate (2.4 g, 6.27 mmol) in CH2Cl2 (30 mL) was added Et3N (1.3 mL, 9.40 mmol), followed by the addition of 3,5-dichloro-2-hydroxybenzenesulfonyl chloride (1.80 g, 6.89 mmol). The reaction mixture was stirred at rt for 2 h. The mixture was diluted with CH2Cl2 and water. The organic layer was washed with saturated NaHCO3 solution, NH4Cl solution, brine solution, and dried over MgSO4. The filtrate was concentrated and the residue was purified by silica gel flash chromatography. The column was eluted with hexane to 80% dichloromethane in hexane. The fractions containing the desired product were combined and concentrated to give colorless viscous solid (2.8 g, 72%).

後処理

  1. washThe organic layer was washed with saturated NaHCO3 solution, NH4Cl solution, brine solution
  2. dry with materialdried over MgSO4
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by silica gel flash chromatography
  5. washThe column was eluted with hexane to 80% dichloromethane in hexane
  6. additionThe fractions containing the desired product
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-8d8afe46468d4085b42d54342236d66c
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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