Triethylamine → Ethyl[2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetate

HRID 733357노트

반응식

HRID 733357 반응식
[NH2:1][CH2:2][CH2:3][C:4]1[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][C:5]=1[O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].C(N(CC)CC)C.[C:27]([C:29]1[CH:30]=[CH:31][C:32]([O:39][CH3:40])=[C:33]([S:35](Cl)(=[O:37])=[O:36])[CH:34]=1)#[N:28]>O1CCCC1.O>[C:27]([C:29]1[CH:30]=[CH:31][C:32]([O:39][CH3:40])=[C:33]([S:35]([NH:1][CH2:2][CH2:3][C:4]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:18])[CH3:19])=[CH:13][C:5]=2[O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:37])=[O:36])[CH:34]=1)#[N:28]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 115287515-Cyano-2-methoxybenzene-1-sulfonyl chlorideHCID 18456985Ethyl[2-(2-aminoethyl)-5-isopropylphenoxy]acetate

생성물 1

HCID 17856206Ethyl[2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetate수율 72.5%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 326 mg of ethyl [2-(2-amino-ethyl)-5-isopropylphenoxy]acetate hydorochloride and 0.452 mL of triethylamine in a mixture of 10 mL of tetrahydrofuran and 5 mL of water was added 238 mg of 5-cyano-2-methoxybenzene-sulfonyl chloride under ice-cooling, and the mixture was stirred at room temperature for 6 hours. To the reaction mixture was added 30 mL of water, and the mixture was extracted with 120 mL of ethyl acetate. The organic layer was washed with 100 mL of water, and 100 mL of brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane) to give 343 mg of ethyl [2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetate.

후처리

  1. temperaturecooling
  2. extractionthe mixture was extracted with 120 mL of ethyl acetate
  3. washThe organic layer was washed with 100 mL of water, and 100 mL of brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-d7a94cbe79894849a397198aad5d2ef8
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589126B2

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