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

HRID 9522

반응식

HRID 9522 반응식
C([NH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:25])[CH2:17][C:18]([CH3:24])([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)=O.Cl>CO>[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:25])[CH2:17][C:18]([CH3:23])([CH3:24])[C:19]([O:21][CH3:22])=[O:20])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 21985799Methyl 4-[4'-(formylamino)-1,1'-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoate

생성물 1

HCID 21985743Methyl 4-(4'-amino-1,1'-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate수율 95.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a suspension of methyl 4-[4′-(formylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoate (2.40 g, 7.07 mmol) in 20 mL methanol, was added 7 mL concentrated hydrochloric acid at below rt. The reaction mixture was stirred at rt overnight. The mixture was concentrated under reduced pressure and saturated aqueous sodium bicarbonate solution was slowly added until pH>8.0. The aqueous layer was then extracted with methylene chloride (2×25 mL), and the combined organic layer was dried over sodium sulfate. The mixture was concentrated under reduced pressure to afford methyl 4-(4′-amino-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate as a light red solid (2.1 g, 95%). 1H NMR (CDCl3) δ 7.96 (d, J=9 Hz, 2H), 7.60 (d, J=9 Hz, 2H), 7.46 (d, J=9 Hz, 2H), 6.76 (d, J=9 Hz, 2H), 3.85 (br s, 2H), 3.69 (s, 3H), 3.32 (s, 2H), 1.35 (s, 6H); ESI-MS m/z 312.4 (MH+); HRMS m/z calcd for MH+312.1594, found 312.1597.

후처리

  1. concentrationThe mixture was concentrated under reduced pressure and saturated aqueous sodium bicarbonate solution
  2. additionwas slowly added until pH>8.0
  3. extractionThe aqueous layer was then extracted with methylene chloride (2×25 mL)
  4. dry with materialthe combined organic layer was dried over sodium sulfate
  5. concentrationThe mixture was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-009a97990c0745b6937ef7f388424e8c
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091228B2

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