Water → 5-(3-chloro-4-cyanophenoxy)-N-(9-ethyl-9H-carbazol-3-yl)-3-hydroxy-3-methylpentanamide

HRID 2272593

반응식

HRID 2272593 반응식
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH:16][C:17](=[O:25])[CH2:18][C:19]([OH:24])([CH3:23])[CH2:20][CH2:21][OH:22])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[Cl:26][C:27]1[CH:34]=[C:33](F)[CH:32]=[CH:31][C:28]=1[C:29]#[N:30].CC(C)([O-])C.[K+].O>C1COCC1>[Cl:26][C:27]1[CH:34]=[C:33]([CH:32]=[CH:31][C:28]=1[C:29]#[N:30])[O:22][CH2:21][CH2:20][C:19]([OH:24])([CH3:23])[CH2:18][C:17]([NH:16][C:12]1[CH:13]=[CH:14][C:15]2[N:3]([CH2:1][CH3:2])[C:4]3[C:9]([C:10]=2[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=3)=[O:25]

참가 물질

6

반응물 4

HCID 962WaterHCID 1090002-Chloro-4-fluorobenzonitrileHCID 23665647Potassium tert-butoxideHCID 86729751N-(9-ethyl-9H-carbazol-3-yl)-3,5-dihydroxy-3-methylpentanamide

생성물 1

HCID 867297525-(3-chloro-4-cyanophenoxy)-N-(9-ethyl-9H-carbazol-3-yl)-3-hydroxy-3-methylpentanamide수율 48.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of the compound obtained in Step 1 (348 mg, 1.02 mmol) and 2-chloro-4-fluorobenzonitrile (159 mg, 1.02 mmol) in THF (10 mL) was added potassium t-butoxide (287 mg, 2.56 mmol), and the mixture was stirred at room temperature for 14 hr. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane) to give the title compound (236 mg, 0.496 mmol, 48.5%) as a white powder.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-26ee037a40c04e91beb60a3cfdc1ab90
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120776B2

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