4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 2-[tert-butoxycarbonyl-(3-fluoro-benzyl)-amino]-ethyl ester

HRID 8639

反応式

HRID 8639 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][C:13]([O:16][C:17](=[O:30])[N:18]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1)[CH2:19][CH2:20][OH:21])([CH3:15])[CH3:14].FC1C=C(C=CC=1)CNCCO.C(N(CC)CC)C>ClCCl>[C:13]([O:16][C:17]([N:18]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1)[CH2:19][CH2:20][O:21][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])=[O:30])([CH3:12])([CH3:14])[CH3:15]

参加物

6

反応物 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 108667492-(3-Fluoro-benzylamino)-ethanolHCID 69653122tert-butyl N-[(3-fluorophenyl)methyl]-N-(2-hydroxyethyl)carbamate

生成物 1

HCID 23548235Toluene-4-sulfonic acid 2-[tert-butoxycarbonyl-(3-fluoro-benzyl)-amino]-ethyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Add p-toluenesulfonyl-chloride (0.71 g, 3.71 mmol), portionwise, to a mixture of (3-fluoro-benzyl)-(2-hydroxy-ethyl)-carbamic acid dimethyl-ethyl ester (1 g, 3.71 mmol, prepared from 2-(3-fluoro-benzylamino)-ethanol by methods as are known in the art), triethylamine (0.751 g, 7.4 mmol) and dichloromethane (6 mL). Stir the resulting suspension vigorously overnight at room temperature. Add water (10 mL), separate the organic layer, and extract the aqueous layer with dichloromethane (5 mL), twice. Combine the organic layers and wash with citric acid (5 mL, 20% in water), dry with sodium sulfate and evaporate the solvent to give the final, desired compound. The final compound may be purified by chromatography.

後処理

  1. customAdd water (10 mL), separate the organic layer
  2. extractionextract the aqueous layer with dichloromethane (5 mL)
  3. washwash with citric acid (5 mL, 20% in water)
  4. dry with materialdry with sodium sulfate
  5. customevaporate the solvent

出典と根拠

ORDレコード
ord-3bfb9478b47f4e919a8a0e2f00a8190d
出典データセット
uspto-grants-2006_08
特許番号
US07091199B1

関連ノート

読み込み中…