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Trifluoroacetic acid → Ethyl 2-(4-(ethylsulfonamidomethyl)-3-fluorophenyl)propanoate

HRID 1428770
ノート
印刷プレビュー

反応式

HRID 1428770 の反応式
Br[C:2]1[CH:14]=[CH:13][C:5]([CH2:6][NH:7][S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])=[C:4]([F:15])[CH:3]=1.Cl[CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19].FC(F)(F)C(O)=O>CN(C)C=O.[Mn]>[CH2:11]([S:8]([NH:7][CH2:6][C:5]1[CH:13]=[CH:14][C:2]([CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:3][C:4]=1[F:15])(=[O:10])=[O:9])[CH3:12]
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

6

反応物 3

HCID 6422Trifluoroacetic acidHCID 10807Ethyl 2-chloropropionateHCID 70816043N-(4-bromo-2-fluorobenzyl)ethanesulfonamide

生成物 1

HCID 70816333Ethyl 2-(4-(ethylsulfonamidomethyl)-3-fluorophenyl)propanoate

試薬・触媒・溶媒 2

HCID 23930Manganese触媒HCID 6228Dimethylformamide
溶媒

反応条件

温度
65 °C

実験手順

To a solution of N-(4-bromo-2-fluorobenzyl)ethanesulfonamide (305 mg, 1.03 mmol) in dimethylformamide, Manganese (113 mg, 2.06 mmol), (2,2′-Bipyridine)nickel(II)-dibromide (27 mg, 0.07 mmol), ethyl 2-chloropropanoate (0.17 mL, 1.34 mmol) was added. It was followed by addition of trifluoroacetic acid (0.002 mL, 0.028 mmol). The mixture was stirred for 24 h at 65° C. The reaction mixture was quenched by concentrated HCl (7 drops). Then it was extracted with diethyl ether, dried over magnesium sulfate, the solvent was evaporated in vacuo. It was purified by column chromatography to obtain ethyl 2-(4-(ethylsulfonamidomethyl)-3-fluorophenyl)propanoate in pure form (65 mg, 20%).

後処理

  1. customThe reaction mixture was quenched by concentrated HCl (7 drops)
  2. extractionThen it was extracted with diethyl ether
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customIt was purified by column chromatography

出典と根拠

ORDレコード
ord-7edd26114cc04e33bfd956ab2d6f7af1
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08937092B2

反応ノート

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