Water → HCID 11351199, 화합물

HRID 11408

반응식

HRID 11408 반응식
[CH2:1]([O:8][C:9]([C:11]1[C:12]2[CH:13]=[C:14]([CH3:20])[NH:15][C:16]=2[CH:17]=[CH:18][CH:19]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:23]([O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1)[CH2:24][CH2:25][CH3:26].O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([C:11]1[C:12]2[CH:13]=[C:14]([CH3:20])[N:15]([C:32](=[O:33])[C:31]3[CH:30]=[CH:29][C:28]([O:27][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:36][CH:35]=3)[C:16]=2[CH:17]=[CH:18][CH:19]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1185614-Butoxybenzoyl chlorideHCID 183550292-Methyindole-4-carboxylic acid benzyl ester

생성물 1

HCID 11351199HCID 11351199, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-methyindole-4-carboxylic acid benzyl ester (690 mg; prepared in Reference Example 11) in N,N-dimethylformamide (8 ml) was added sodium hydride (114 mg; 60%) at 0° C., and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture was added 4-butoxybenzoyl chloride (0.54 ml), and the mixture was stirred at room temperature overnight. To the reaction mixture was added water and ethyl acetate, and then separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and a saturated aqueous solution of sodium chloride, successively, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane-ethyl acetate) to give the title compound (1.02 g) having the following physical data.

후처리

  1. stirringthe mixture was stirred at room temperature overnight
  2. customseparated
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride, successively, dried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-9c82ce6bb1624d23822093bef6f2b185
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098234B2

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