Potassium Carbonate → Isohexane ethyl acetate

HRID 1677879ノート

反応式

HRID 1677879 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:18]2[C:19]([OH:25])=[CH:20][CH:21]=[C:22]([F:24])[CH:23]=2)[CH:5]=[CH:6][C:7]=1[S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])(=[O:10])=[O:9].CC1C=CC(S([O:36][C@H:37]([CH3:42])[C:38]([O:40][CH3:41])=[O:39])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH3:7][CH2:2][CH2:3][CH:4]([CH3:18])[CH3:5].[C:37]([O:25][CH2:19][CH3:20])(=[O:36])[CH3:38].[F:1][C:2]1[CH:3]=[C:4]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[O:25][C@@H:37]([CH3:42])[C:38]([O:40][CH3:41])=[O:39])[CH:5]=[CH:6][C:7]=1[S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])(=[O:10])=[O:9]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 12884153(R)-2-Tosyloxypropionic acid methyl esterHCID 672415383',5-Difluoro-4'-[(2-fluorophenyl)sulfonyl]biphenyl-2-ol

生成物 2

HCID 21882781Isohexane ethyl acetateHCID 67240103Methyl (2s)-2-({3',5-difluoro-4'-[(2-fluorophenyl)sulfonyl]biphenyl-2-yl}oxy)propanoate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
65 °C

実験手順

The product of step (v) (175 mg), the product of step (vi) (124 mg) and potassium carbonate (133 mg) in acetonitrile (10 ml) were charged to a flask and stirred at 65° C. overnight. The reaction mixture was cooled, diluted with water (20 ml) and extracted with diethyl ether. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by chromatography on silica eluting with isohexane then 4:1 isohexane/ethyl acetate to give the sub-title compound as a colourless oil, yield 121 mg.

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with diethyl ether
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica eluting with isohexane

出典と根拠

ORDレコード
ord-00c800cf13864507bdb9681f9f72b22d
出典データセット
uspto-grants-2011_08
特許番号
US08008350B2

反応ノート

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