Ethyl Acetate → 4-[2-(tert-Butoxycarbonylamino)ethoxy]-3-methoxy-N-[3-[(E)-2-(3-methylphenyl)vinyl]phenyl]phenylacetamide

HRID 7082

반응식

HRID 7082 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24](I)[CH:23]=2)=[O:20])=[CH:14][C:13]=1[O:29][CH3:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[CH:32]=[CH:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1.[CH3:40]C1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(OCC)(=O)C>CN(C)C=O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24](/[CH:32]=[CH:33]/[C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([CH3:40])[CH:35]=3)[CH:23]=2)=[O:20])=[CH:14][C:13]=1[O:29][CH3:30])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 12500beta-MethylstyreneHCID 80271Tri-o-tolylphosphineHCID 220196094-[2-(tert-butoxycarbonylamino)ethoxy]-N-(3-iodophenyl)-3-methoxyphenylacetamide

생성물 1

HCID 220195834-[2-(tert-Butoxycarbonylamino)ethoxy]-3-methoxy-N-[3-[(E)-2-(3-methylphenyl)vinyl]phenyl]phenylacetamide수율 152.4%

시약·촉매·용매 3

HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
97 °C

실험 절차

Intermediate 4 (1 g) is dissolved in dimethylformamide (10 ml), and thereto are added 3-methylvinylbenzene (826 mg), palladium (II) acetate (105 mg), tris(2-methylphenyl)phosphine (143 mg), tetra-n-butyl ammonium chloride (130 mg), and the mixture is heated with stirring at 97° C. for 18 hours under argon atmosphere. To the reaction solution is added ethyl acetate, and the mixture is washed with water and 2 M hydrochloric acid. The organic layer is dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give 4-[2-(tert-butoxycarbonylamino)-ethoxy]-3-methoxy-N-[3-[(E)-2-(3-methylphenyl)vinyl]phenyl]phenylacetamide (370 mg). This product is treated with 10% hydrogen chloride-methanol to give the desired compound (120 mg).

후처리

  1. temperaturethe mixture is heated
  2. washthe mixture is washed with water and 2 M hydrochloric acid
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. customthe solvent is evaporated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-75cc4b5bd19f4a4696cb5248dd41f0c1
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084176B2

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