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

HRID 1428727노트

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HRID 1428727 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 6422Trifluoroacetic acid촉매HCID 23930Manganese촉매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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). Trifluoroacetic acid (2 drops) was 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 was removed in vacuo. The crude was purified by column chromatography to obtain ethyl 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoate (218 mg).

후처리

  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 was removed in vacuo
  6. customThe crude was purified by column chromatography

출처 및 근거

ORD 기록
ord-9393fb64e4fb4ed1a590ce015091ef73
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937092B2

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