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Trifluoroacetic acid → 2-(4-(Ethylsulfonamidomethyl)-3-fluorophenyl)propanoic acid

HRID 1842987
ノート
印刷プレビュー

反応式

HRID 1842987 の反応式
[CH2:1]([S:3]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:20])[C:15]([O:17]CC)=[O:16])=[CH:10][C:9]=1[F:21])(=[O:5])=[O:4])[CH3:2].C(O)(C(F)(F)F)=O>CN(C=O)C.[Mn]>[CH2:1]([S:3]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:20])[C:15]([OH:17])=[O:16])=[CH:10][C:9]=1[F:21])(=[O:5])=[O:4])[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

5

反応物 2

HCID 6422Trifluoroacetic acidHCID 70816333Ethyl 2-(4-(ethylsulfonamidomethyl)-3-fluorophenyl)propanoate

生成物 1

HCID 708165692-(4-(Ethylsulfonamidomethyl)-3-fluorophenyl)propanoic acid

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 ethyl 2-(4-(ethylsulfonamidomethyl)-3-fluorophenyl)propanoate (305 mg, 1.03 mmol) in DMF, manganese (113 mg, 2.06 mmol), NiBr2bipy (27 mg, 0.07 mmol), ethyl-2-chloro propionate (0.17 mL, 1.34 mmol) was added, followed by addition of TFA (0.002 mL, 0.028 mmol). The mixture was stirred for 1 day at 65° C. The reaction mixture was quenched by conc. HCl (7-drops) and then extracted with diethyl ether, dried (MgSO4) and the solvent was evaporated in vacuo. The residue was purified by CC (EtOAc/n-hexane). 2-(4-(ethyl-sulfonamidomethyl)-3-fluorophenyl)propanoic acid in pure form (65 mg, 20%) was obtained.

後処理

  1. customThe reaction mixture was quenched by conc. HCl (7-drops)
  2. extractionextracted with diethyl ether
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by CC (EtOAc/n-hexane)

出典と根拠

ORDレコード
ord-5a0a674743504fb2a83b21ff1159eeaf
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08946204B2

反応ノート

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