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

HRID 1912084노트

반응식

HRID 1912084 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f4572a9c65654a82986edaddda496f23
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604069B2

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