Tetrahydrofuran → {2-[3-(t-Butoxycarbonylaminomethyl)-4-cyanophenylimino]-2-(5-ethyl-2-fluoro-3-hydroxyphenyl)-1-methylsulfanylethylidene}carbamic Acid Methyl Ester

HRID 1157952ノート

反応式

HRID 1157952 の反応式
[CH3:1][O:2][C:3](=[O:47])[N:4]=[C:5]([S:45][CH3:46])[C:6](=[N:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[C:30]([CH2:36][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH:29]=1)[C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]([O:15][Si](C(C)C)(C(C)C)C(C)C)[C:8]=1[F:26].C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>O>[CH3:1][O:2][C:3](=[O:47])[N:4]=[C:5]([S:45][CH3:46])[C:6](=[N:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[C:30]([CH2:36][NH:37][C:38]([O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:39])[CH:29]=1)[C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]([OH:15])[C:8]=1[F:26]

参加物

6

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 72311201{2-[3-(t-Butoxycarbonylaminomethyl)-4-cyanophenylimino]-2-(5-ethyl-2-fluoro-3-triisopropylsilanyloxyphenyl)-1-methylsulfanylethylidene}carbamic acid methyl ester

生成物 1

HCID 72311195{2-[3-(t-Butoxycarbonylaminomethyl)-4-cyanophenylimino]-2-(5-ethyl-2-fluoro-3-hydroxyphenyl)-1-methylsulfanylethylidene}carbamic Acid Methyl Ester収率 85.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of {2-[3-(t-butoxycarbonylaminomethyl)-4-cyanophenylimino]-2-(5-ethyl-2-fluoro-3-triisopropylsilanyloxyphenyl)-1-methylsulfanylethylidene}carbamic acid methyl ester (523 mg) and THF (10 mL) there was added a 1M THF solution of tetrabutylammonium fluoride (1.56 mL) under a nitrogen atmosphere. The mixture was stirred for 90 minutes, and then ethyl acetate (300 mL) and water (100 mL) were added. The mixture was sufficiently shaken, and then the organic layer was separated off, washed twice with water (100 mL) and once with saturated aqueous sodium chloride (100 mL) in that order, and dried over anhydrous magnesium sulfate. The mixture was filtered to obtain a filtrate, and the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture) to obtain the target compound (346 mg) as a colorless solid.

後処理

  1. stirringThe mixture was sufficiently shaken
  2. customthe organic layer was separated off
  3. washwashed twice with water (100 mL) and once with saturated aqueous sodium chloride (100 mL) in that order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe mixture was filtered
  6. customto obtain a filtrate
  7. distillationthe solvent in the filtrate was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture)

出典と根拠

ORDレコード
ord-2b9215bb5fab4d659983f01b763bac00
出典データセット
uspto-grants-2010_10
特許番号
US07807690B2

反応ノート

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