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

HRID 877238ノート

反応式

HRID 877238 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fc17cb3a2ffd48fd999822ee5691d13e
出典データセット
uspto-grants-2015_03
特許番号
US08987256B2

反応ノート

読み込み中…