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

HRID 1428713노트

반응식

HRID 1428713 반응식
Br[C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl[CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].Cl>CN(C)C=O.FC(F)(F)C(O)=O.[Mn]>[CH3:11][S:8]([NH:7][CH2:6][C:5]1[CH:12]=[CH:13][C:2]([CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 10807Ethyl 2-chloropropionateHCID 19027423N-[(4-bromophenyl)methyl]methanesulfonamide

생성물 1

HCID 70816013Ethyl 2-(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-bromobenzyl)methanesulfonamide (675 mg, 2.555 mmol) in dimethylformamide were added ethyl 2-chloropropionate (0.42 mL), manganese (280 mg) and (2,2′-bipyridine)nickel(II)-dibromide (67 mg, 0.17885 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 removed in vacuo. The crude was purified by column chromatography to obtain ethyl 2-(4-(methylsulfonamidomethyl)phenyl)propanoate (325 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 removed in vacuo
  6. customThe crude was purified by column chromatography

출처 및 근거

ORD 기록
ord-416544318e194d2bb5f564fc25217aea
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937092B2

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