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

HRID 1962863ノート

反応式

HRID 1962863 の反応式
[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]

参加物

5

反応物 2

HCID 11430Potassium CarbonateHCID 68422187HCID 68422187、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8079e661de884cfb9504423f495d275c
出典データセット
uspto-grants-2013_04
特許番号
US08415272B2

反応ノート

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