Potassium Carbonate → 2-(3-ethynyl-8-methyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide

HRID 1962863노트

반응식

HRID 1962863 반응식
[OH:1][CH2:2][C:3]([NH:8][C:9](=[O:31])[CH:10]([S:29][CH3:30])[O:11][C:12]1[CH:13]=[C:14]2[C:19](=[C:20]([CH3:22])[CH:21]=1)[N:18]=[CH:17][C:16]([C:23]#[C:24][Si](C)(C)C)=[CH:15]2)([CH2:5][O:6][CH3:7])[CH3:4].C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C>[C:23]([C:16]1[CH:17]=[N:18][C:19]2[C:14]([CH:15]=1)=[CH:13][C:12]([O:11][CH:10]([S:29][CH3:30])[C:9]([NH:8][C:3]([CH2:5][O:6][CH3:7])([CH3:4])[CH2:2][OH:1])=[O:31])=[CH:21][C:20]=2[CH3:22])#[CH:24]

참가 물질

5

반응물 2

HCID 11430Potassium CarbonateHCID 68422187HCID 68422187, 화합물

생성물 1

HCID 595653242-(3-ethynyl-8-methyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide수율 87.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-2-(8-methyl-3-trimethylsilanylethynyl-quinolin-6-yloxy)-acetamide (650 mg) in methanol (16 ml) was treated with potassium carbonate (97 mg) at room temperature. The reaction mixture was stirred for 1 h. The reaction mixture was diluted with ethyl acetate and washed with sat. aq. sodium hydrogen carbonate. The aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography (cyclohexane/ethyl acetate/dichloromethane 2:2:1) to give 2-(3-ethynyl-8-methyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide (480 mg) as a white solid as mixture of diastereoisomers.

후처리

  1. washwashed with sat. aq. sodium hydrogen carbonate
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (cyclohexane/ethyl acetate/dichloromethane 2:2:1)

출처 및 근거

ORD 기록
ord-8079e661de884cfb9504423f495d275c
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415272B2

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