Hydrochloric Acid → Ethyl 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoate

HRID 1428723ノート

反応式

HRID 1428723 の反応式
Br[C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[C:4]([F:14])[CH:3]=1.Cl[CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18].Cl>CN(C)C=O.FC(F)(F)C(O)=O.[Mn]>[F:14][C:4]1[CH:3]=[C:2]([CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=[CH:12][C:5]=1[CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 10807Ethyl 2-chloropropionateHCID 70847718N-(4-bromo-2-fluorobenzyl)methanesulfonamide

生成物 1

HCID 70855559Ethyl 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoate

試薬・触媒・溶媒 3

HCID 6422Trifluoroacetic acid触媒HCID 23930Manganese触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of N-(4-bromo-2-fluorobenzyl)methanesulfonamide (2.94 g, 10.421 mmol) in dimethylformamide were added ethyl 2-chloropropionate (1.725 mL), manganese (1.145 g) and (2,2′-bipyridine)nickel(II)-dibromide (273 mg, mmol). 1-2 drops trifluoroacetic acid were added. The reaction mixture was stirred for 36 h at 60° C. After cooling down to room temperature, the mixture was hydrolysed by 1N HCl and extracted with diethyl ether. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. Ethyl 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoate (218 mg) was obtained.

後処理

  1. temperatureAfter cooling down to room temperature
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate removed in vacuo
  6. customThe crude was purified by column chromatography

出典と根拠

ORDレコード
ord-afcb9a61fe6d4b4989e1f8b3adbbaf2d
出典データセット
uspto-grants-2015_01
特許番号
US08937092B2

反応ノート

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