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Ethyl(methoxy)amine hydrochloride → 2-tert-Butyl-6-chloro-benzooxazole-7-sulfonic acid ethyl-methoxy-amide

HRID 516918
ノート
印刷プレビュー

反応式

HRID 516918 の反応式
Cl.[CH2:2]([NH:4][O:5][CH3:6])[CH3:3].[C:7]([C:11]1[O:12][C:13]2[C:19]([S:20](Cl)(=[O:22])=[O:21])=[C:18]([Cl:24])[CH:17]=[CH:16][C:14]=2[N:15]=1)([CH3:10])([CH3:9])[CH3:8]>C1COCC1.CCOC(C)=O>[CH2:2]([N:4]([O:5][CH3:6])[S:20]([C:19]1[C:13]2[O:12][C:11]([C:7]([CH3:9])([CH3:8])[CH3:10])=[N:15][C:14]=2[CH:16]=[CH:17][C:18]=1[Cl:24])(=[O:21])=[O:22])[CH3:3]
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

5

反応物 2

HCID 22613948Ethyl(methoxy)amine hydrochloride2 回HCID 234477912-Tert-butyl-6-chlorobenzoxazole-7-sulfonyl chloride

生成物 1

HCID 866386352-tert-Butyl-6-chloro-benzooxazole-7-sulfonic acid ethyl-methoxy-amide

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

N-Ethyl-O-methylhydroxylamine hydrochloride (Intermediate G) (3.39 g, 30.4 mmol) was suspended in dry THF (20 ml) and cooled to 0° C. in an ice bath while stirring. TEA (4.24 ml, 30.4 mmol) was added followed by dropwise addition of 2-tert-butyl-6-chloro-benzooxazole-7-sulfonyl chloride (US 2007/0249672 page 9) (4.68 g, 15.19 mmol) in THF (10 ml) over 2.5 hours. The reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with EtOAc and washed with H2O, brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography, eluting with 0-10% EtOAc in iso-hexane, to yield a white solid [M+H]+ 347.2

後処理

  1. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  2. washwashed with H2O, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography
  6. washeluting with 0-10% EtOAc in iso-hexane
  7. customto yield a white solid [M+H]+ 347.2

出典と根拠

ORDレコード
ord-e43f30ff305f4246bd01404c4c74edba
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09115087B2

反応ノート

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