Ethyl chloroformate → Ethyl [5-methoxy-2-(6-methoxy-3,4-dihydronaphthalen-2-yl)phenyl]carbamate

HRID 1950142노트

반응식

HRID 1950142 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=3)[CH:11]=2)=[C:7]([NH2:9])[CH:8]=1.[C:22](Cl)(=[O:26])[O:23][CH2:24][CH3:25].[Cl-].[NH4+]>O1CCCC1.C(N(CC)C(C)C)(C)C>[CH2:24]([O:23][C:22](=[O:26])[NH:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[C:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=2)[CH:11]=1)[CH3:25]

참가 물질

6

반응물 3

HCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 230872185-Methoxy-2-(6-methoxy-3,4-dihydronaphthalen-2-yl)phenylamine

생성물 1

HCID 86605239Ethyl [5-methoxy-2-(6-methoxy-3,4-dihydronaphthalen-2-yl)phenyl]carbamate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 81531Diisopropylethylamine용매

실험 절차

To a solution of 5-methoxy-2-(6-methoxy-3,4-dihydronaphthalen-2-yl)phenylamine (400 mg) in tetrahydrofuran (10 ml) and N,N-diisopropylethylamine (0.5 ml) was added ethyl chlorocarbonate (0.2 ml) on an ice bath, and the solution was stirred overnight at room temperature. A saturated aqueous solution of ammonium chloride was added thereto, the solution was extracted with ethyl acetate, then sequentially washed with water and brine, and the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide ethyl[5-methoxy-2-(6-methoxy-3,4-dihydronaphthalen-2-yl)phenyl]carbamate (445 mg). This compound (438 mg) was used according to an analogous synthetic method to Example 337 described below to provide the title compound (286 mg).

후처리

  1. extractionthe solution was extracted with ethyl acetate
  2. washsequentially washed with water and brine
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

출처 및 근거

ORD 기록
ord-878abe98d9b44493b868f2017bf6155c
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399520B2

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