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(Diethylamino)sulfur trifluoride → HCID 118253466、化合物

HRID 921892
ノート
印刷プレビュー

反応式

HRID 921892 の反応式
[C:1]([O:5][C:6]([N:8]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[C:9]1[C:10]([Cl:29])=[C:11]([C:17]2(O)[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]2)[CH:12]=[C:13]([C:15]#[N:16])[CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(S(F)(F)[F:45])CC)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[C:9]1[C:10]([Cl:29])=[C:11]([C:17]2([F:45])[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]2)[CH:12]=[C:13]([C:15]#[N:16])[CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 89922436Tert-butyl 3-(3-((tert-butoxycarbonyl)(4-methoxybenzyl)amino)-2-chloro-5-cyanophenyl)-3-hydroxyazetidine-1-carboxylate

生成物 1

HCID 118253466HCID 118253466、化合物収率 78.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of tert-butyl 3-(3-((tert-butoxycarbonyl)(4-methoxybenzyl)amino)-2-chloro-5-cyanophenyl)-3-hydroxyazetidine-1-carboxylate (408 mg, 0.75 mmol) in dry CH2Cl2 (12 mL) at −78° C. under nitrogen was added diethylaminosulfur trifluoride (153 μL, 0.90 mmol). The mixture was allowed to warm to 0° C. over 4 h and quenched by adding 1M aqueous NaOH at −5° C. The reaction mixture was diluted with EtOAc, washed with water, brine, and dried over sodium sulfate. Solvent was removed. The residue was purified by ISCO column (12 g) chromatography, eluting with hexane containing 0 to 40% EtOAc to afford tert-butyl 3-(3-((tert-butoxycarbonyl)(4-methoxybenzyl)amino)-2-chloro-5-cyanophenyl)-3-fluoroazetidine-1-carboxylate (321 mg).

後処理

  1. customquenched
  2. additionby adding 1M aqueous NaOH at −5° C
  3. additionThe reaction mixture was diluted with EtOAc
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customSolvent was removed
  7. customThe residue was purified by ISCO column (12 g) chromatography
  8. washeluting with hexane containing 0 to 40% EtOAc

出典と根拠

ORDレコード
ord-fe18b8e4cdcf4853bd8bb5a595d31722
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09273057B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート