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4-Chloro-2-toluidine → Methyl 5-(4-chloro-2-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valerate

HRID 1912081
ノート
印刷プレビュー

反応式

HRID 1912081 の反応式
[CH:1]1([C:4]2[C:5]([CH:18]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH2:19][C:20]([O-])=[O:21])=[N:6][O:7][C:8]=2[CH:9]2[CH2:12][CH:11]([CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:10]2)[CH2:3][CH2:2]1.[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([NH2:36])=[C:32]([CH3:37])[CH:31]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(=O)(O)[O-].[Na+]>O.CN(C=O)C>[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:20]([CH2:19][CH:18]([C:5]2[C:4]([CH:1]3[CH2:3][CH2:2]3)=[C:8]([CH:9]3[CH2:12][CH:11]([CH2:13][C:14]([CH3:17])([CH3:15])[CH3:16])[CH2:10]3)[O:7][N:6]=2)[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[O:21])=[C:32]([CH3:37])[CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 72514-Chloro-2-toluidineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866750456-Methyl 3-[4-Cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl]adipate

生成物 1

HCID 71114755
Methyl 5-(4-chloro-2-methylphenylcarbamoyl)-4-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}valerate
収率 55.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

6-Methyl 3-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl}adipate (100 mg), 4-chloro-2-methylphenylamine (43.5 mg) and DMF (1 mL) were mixed. To the mixture were added HOBt.H2O (47 mg) and WSC.HCl (58.8 mg) at ice temperature. The mixture was stirred at RT, and further stirred at 70° C. To the reaction mixture was added saturated aqueous sodium bicarbonate 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: ethyl acetate/hexane=1/4) to give the title compound (72.8 mg).

後処理

  1. stirringfurther stirred at 70° C
  2. extractionThe mixture was extracted 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: ethyl acetate/hexane=1/4)

出典と根拠

ORDレコード
ord-831a49d868c0430fadbeb33b70446c17
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…

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