Acetic Acid → 5-(2-Chloro-4-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valeric acid

HRID 1912084ノート

反応式

HRID 1912084 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([CH2:12][CH:13]([C:20]1[C:24]([CH:25]2[CH2:27][CH2:26]2)=[C:23]([CH:28]2[CH2:31][CH:30]([CH2:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:29]2)[O:22][N:21]=1)[CH2:14][CH2:15][C:16]([O:18]C)=[O:17])=[O:11].C(O)(=O)C.Br.C([O-])(=O)C.[Na+]>O>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([CH2:12][CH:13]([C:20]1[C:24]([CH:25]2[CH2:26][CH2:27]2)=[C:23]([CH:28]2[CH2:29][CH:30]([CH2:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:31]2)[O:22][N:21]=1)[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:11]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 517045Sodium AcetateHCID 71114721Methyl 5-(2-chloro-4-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valerate

生成物 1

HCID 711147225-(2-Chloro-4-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valeric acid収率 92.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Methyl 5-(2-chloro-4-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valerate (63.3 mg) and acetic acid (0.6 mL) were mixed. To the mixture was added 48 w/v % hydrobromic acid (0.3 mL) at 10° C. The mixture was stirred at RT, and further stirred at 50° C. To the reaction mixture were added sodium acetate (250 mg) and water at ice temperature. The mixture was extracted twice with ethyl acetate. The organic layer was washed with water and brine, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo. The resultant residue was purified by preparative chromatography (Eluent: methanol/chloroform/acetic acid=1/20/0.1) to give the title compound (56.7 mg).

後処理

  1. stirringfurther stirred at 50° C
  2. extractionThe mixture was extracted twice with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe magnesium sulfate was filtered off
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe resultant residue was purified by preparative chromatography (Eluent: methanol/chloroform/acetic acid=1/20/0.1)

出典と根拠

ORDレコード
ord-f4572a9c65654a82986edaddda496f23
出典データセット
uspto-grants-2013_12
特許番号
US08604069B2

反応ノート

読み込み中…