Water → ethyl 4,4,4-trifluoro-3-methyl-2-{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}butanoate

HRID 877238노트

반응식

HRID 877238 반응식
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.[H-].[Na+].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([CH:27]([CH3:32])[C:28]([F:31])([F:30])[F:29])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:16]=1.O>CN(C=O)C.C(OCC)(=O)C>[F:29][C:28]([F:30])([F:31])[CH:27]([CH3:32])[CH:21]([C:18]1[CH:17]=[CH:16][C:15]([CH2:14][N:2]2[CH2:3][C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:1]2=[O:10])=[CH:20][CH:19]=1)[C:22]([O:24][CH2:25][CH3:26])=[O:23]

참가 물질

7

반응물 4

HCID 962WaterHCID 10199PhthalimidineHCID 24758Sodium hydrideHCID 58136537Ethyl 2-[4-(bromomethyl)phenyl]-4,4,4-trifluoro-3-methylbutanoate

생성물 1

HCID 58136395ethyl 4,4,4-trifluoro-3-methyl-2-{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}butanoate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

At 0° C., 222.6 mg (1.67 mmol) of 2,3-dihydro-1H-isoindol-1-one were added to 66.9 mg (1.67 mmol, 60% pure) of sodium hydride in 2 ml of DMF. The mixture was stirred for 30 min, and 600 mg (1.39 mmol) of ethyl 2-[4-(bromomethyl)phenyl]-4,4,4-trifluoro-3-methylbutanoate were then added at 0° C. The reaction mixture was stirred for a further 2 h, and water and ethyl acetate were then added. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulfate. The crude product was purified by preparative RP-HPLC (mobile phase: acetonitrile/water gradient). This gave 108 mg (19% of theory) of the target compound.

후처리

  1. stirringThe reaction mixture was stirred for a further 2 h
  2. washThe organic phase was washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customThe crude product was purified by preparative RP-HPLC (mobile phase: acetonitrile/water gradient)

출처 및 근거

ORD 기록
ord-fc17cb3a2ffd48fd999822ee5691d13e
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987256B2

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