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

HRID 1912082
ノート
印刷プレビュー

反応式

HRID 1912082 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH2:11][CH:12]([C:19]2[C:23]([CH:24]3[CH2:26][CH2:25]3)=[C:22]([CH:27]3[CH2:30][CH:29]([CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:28]3)[O:21][N:20]=2)[CH2:13][CH2:14][C:15]([O:17]C)=[O:16])=[O:10])=[C:4]([CH3:36])[CH:3]=1.Br.C([O-])(=O)C.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH2:11][CH:12]([C:19]2[C:23]([CH:24]3[CH2:25][CH2:26]3)=[C:22]([CH:27]3[CH2:28][CH:29]([CH2:31][C:32]([CH3:34])([CH3:33])[CH3:35])[CH2:30]3)[O:21][N:20]=2)[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:10])=[C:4]([CH3:36])[CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 260Hydrogen BromideHCID 517045Sodium AcetateHCID 71114755Methyl 5-(4-chloro-2-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valerate

生成物 1

HCID 711147445-(4-Chloro-2-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valeric acid収率 69.6%

試薬・触媒・溶媒 1

HCID 176
Acetic Acid
溶媒

反応条件

温度
60 °C

実験手順

Methyl 5-(4-chloro-2-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valerate (72.5 mg) and acetic acid (0.725 mL) were mixed. To the mixture was added 48 w/v % hydrobromic acid (0.363 mL) at RT. The mixture was stirred at 60° C., and then to the reaction mixture was added sodium acetate (287 mg) at ice temperature. The mixture was extracted 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=1/20/0.05) to give the title compound (49.1 mg). The specific optical rotation value of the title compound was [α]D25=+32.0° (c=1.00, methanol). The title compound was analyzed using a chiral column. The retention time of the title compound was 26.8 min., and the optical purity thereof was 94.8% ee.

後処理

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe resultant residue was purified by preparative chromatography (Eluent: methanol/chloroform/acetic acid=1/20/0.05)

出典と根拠

ORDレコード
ord-87a47da439664b3ab572411747fd9dbf
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08604069B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート