Tert-butyl 4-isothiocyanatopiperidine-1-carboxylate → tert-Butyl 4-(3-((3SR,5SR)-3-(2-chloro-4-fluorophenyl)-5-hydroxy-2-oxopiperidin-1-yl)thioureido)piperidine-1-carboxylate

HRID 451522ノート

反応式

HRID 451522 の反応式
[NH2:1][N:2]1[CH2:7][CH:6]([OH:8])[CH2:5][CH:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[Cl:16])[C:3]1=[O:17].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([N:31]=[C:32]=[S:33])[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>CC(N(C)C)=O.C(OCC)(=O)C>[Cl:16][C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[CH:4]1[CH2:5][CH:6]([OH:8])[CH2:7][N:2]([NH:1][C:32](=[S:33])[NH:31][CH:28]2[CH2:27][CH2:26][N:25]([C:23]([O:22][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:24])[CH2:30][CH2:29]2)[C:3]1=[O:17]

参加物

5

反応物 2

HCID 58591952Tert-butyl 4-isothiocyanatopiperidine-1-carboxylateHCID 67344225(3SR,5SR)-1-Amino-3-(2-chloro-4-fluorophenyl)-5-hydroxypiperidin-2-one

生成物 1

HCID 86656717tert-Butyl 4-(3-((3SR,5SR)-3-(2-chloro-4-fluorophenyl)-5-hydroxy-2-oxopiperidin-1-yl)thioureido)piperidine-1-carboxylate収率 83%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of (3SR,5SR)-1-amino-3-(2-chloro-4-fluorophenyl)-5-hydroxypiperidin-2-one (0.8 g, 2.9 mmol) in dimethylacetamide (1 mL) was added 4-isothiocyanatopiperidine-1-carboxylic acid tert-butyl ester (0.8 g, 3.2 mmol, US2006/14958A1) and the reaction stirred for 2 hours at 80° C. The reaction was diluted with ethyl acetate, washed with water, brine, dried with sodium sulfate and the solvent was evaporated in vacuo. The product was triturated from dichloromethane by addition of heptane to afford the title compound as a colourless powder (1.2 g, 83%). MS ISP (m/e): 501.2 [(M+H)+].

後処理

  1. washwashed with water, brine
  2. dry with materialdried with sodium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customThe product was triturated from dichloromethane by addition of heptane

出典と根拠

ORDレコード
ord-7a638818a2e947d88a34a747fd171dd0
出典データセット
uspto-grants-2013_07
特許番号
US08486967B2

反応ノート

読み込み中…