Ethanol → Ethyl 2-amino-2-(4-fluorophenyl)acetate

HRID 451134노트

반응식

HRID 451134 반응식
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].OS(O)(=O)=O.[CH2:18](O)[CH3:19]>>[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[C:3]([O:5][CH2:18][CH3:19])=[O:4]

참가 물질

4

반응물 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 98313(1)-4-Fluorophenylglycine

생성물 1

HCID 5178419Ethyl 2-amino-2-(4-fluorophenyl)acetate수율 65%

실험 절차

To a cooled solution of 2-amino-2-(4-fluorophenyl)acetic acid (1.0 g, 6.17 mmol) in ethanol was added con. H2SO4 (1 mL) over a period of 1 min. The reaction mixture was heated at reflux for 5 h. The solvent was evaporated under reduced pressure and the residue was diluted with ethyl acetate (20 mL). The organic solution was washed with aqueous saturated NaHCO3 (15 mL×2), water (20 mL), brine solution (10 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure to give ethyl 2-amino-2-(4-fluorophenyl)acetate (0.75 g, 65%) as crude compound (oily liquid). The crude compound was taken to the next step without further purification. LC-MS (M+H2O)+=198.0. 1H NMR (400 MHz, DMSO-d6): δ 7.44-7.40 (2H, m), 7.18-7.13 (2H, m), 4.51 (1H, s), 4.12-4.01 (2H, m), 2.26 (2H, s), 1.12 (3H, t, J=8.0 Hz).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5 h
  3. customThe solvent was evaporated under reduced pressure
  4. additionthe residue was diluted with ethyl acetate (20 mL)
  5. washThe organic solution was washed with aqueous saturated NaHCO3 (15 mL×2), water (20 mL), brine solution (10 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-81f39d8a563d41ffb36613701093d848
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486952B2

반응 노트

불러오는 중…