Hydrochloric Acid → Methyl 4-(4'-amino-3'-fluoro-1,1'-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate

HRID 9555

반응식

HRID 9555 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17](=[O:26])[CH2:18][C:19]([CH3:25])([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[NH:8]C=O.Cl>CO>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([C:11]2[CH:12]=[CH:13][C:14]([C:17](=[O:26])[CH2:18][C:19]([CH3:24])([CH3:25])[C:20]([O:22][CH3:23])=[O:21])=[CH:15][CH:16]=2)=[CH:3][C:2]=1[F:1]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 21985807Methyl 4-[3'-fluoro-4'-(formylamino)-1,1'-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoate

생성물 1

HCID 21985864Methyl 4-(4'-amino-3'-fluoro-1,1'-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate수율 89.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of methyl 4-[3′-fluoro-4′-(formylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoate (1.21 g, 3.39 mmol) in methanol (10 mL) was added conc. HCl (3.5 mL), and the resulting solution was stirred at rt for 16 h. The mixture was then concentrated, diluted with water, and the acidity was adjusted to pH ˜7 by slow addition of saturated aqueous sodium bicarbonate solution. The mixture was then extracted with dichloromethane, and the combined organic layers were washed with saturated sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure. The residue was then triturated with ethyl acetate/hexane to afford methyl 4-(4′-amino-3′-fluoro-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate (998 mg, 89%). LC-MS ret. time 3.11 min, m/z 329.9 (MH+); 1H NMR (300 MHz, CDCl3) δ 1.31 (s, 6H), 3.28 (s, 2H), 3.66 (s, 3H), 6.84 (t, 1H), 7.21–7.35 (m, 2H), 7.55 (d, 2H), 7.93 (d, 2H).

후처리

  1. concentrationThe mixture was then concentrated
  2. additiondiluted with water
  3. additionthe acidity was adjusted to pH ˜7 by slow addition of saturated aqueous sodium bicarbonate solution
  4. extractionThe mixture was then extracted with dichloromethane
  5. washthe combined organic layers were washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was then triturated with ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-a825343b56b045bc88ebcee19973a6ae
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091228B2

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