Ethyl Acetate → (S)-4-isopropyl-3-(2-(((S)-1-(5-phenyl-1,3,4-oxadiazol-2-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one

HRID 1850216ノート

反応式

HRID 1850216 の反応式
C(O[C:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(OCC)OCC)C.[CH:17]([C@H:20]1[CH2:24][O:23][C:22](=[O:25])[N:21]1[C:26]1[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C@@H:33]([CH3:38])[C:34]([NH:36][NH2:37])=[O:35])[N:27]=1)([CH3:19])[CH3:18].C(OCC)(=O)C>CCCCCCC>[CH:17]([C@H:20]1[CH2:24][O:23][C:22](=[O:25])[N:21]1[C:26]1[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C@H:33]([C:34]2[O:35][C:4]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:37][N:36]=2)[CH3:38])[N:27]=1)([CH3:19])[CH3:18]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 74268Benzene, (triethoxymethyl)-HCID 86730168(S)-2-((4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-yl)amino)propanehydrazide

生成物 1

HCID 86730271(S)-4-isopropyl-3-(2-(((S)-1-(5-phenyl-1,3,4-oxadiazol-2-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one収率 17.9%

試薬・触媒・溶媒 1

HCID 8900Heptane溶媒

実験手順

A solution of (triethoxymethyl)benzene (360 mg, 1.6 mmol, 5.0 equiv. in 5 mL of benzene and 0.5 mL of glacial AcOH) was added to (S)-2-((4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-yl)amino)propanehydrazide (99 mg, 0.30 mmol, 1.0 equiv.), the reaction mixture was stirred at reflux for 1.5 hours, the solvent was removed to yield the crude product. Silica gel column chromatography (ethyl acetate in heptane 10 to 90%) to yield (S)-4-isopropyl-3-(2-(((S)-1-(5-phenyl-1,3,4-oxadiazol-2-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one (21.2 mg, white solid) in 15.9% yield. HRMS(B) m/z 395.1820, (M+H)+, RT=2.42 min

後処理

  1. temperatureat reflux for 1.5 hours
  2. customthe solvent was removed
  3. customto yield the crude product

出典と根拠

ORDレコード
ord-570d6f198e06499fa4b3f4a5410e5e3c
出典データセット
uspto-grants-2015_02
特許番号
US08957068B2

反応ノート

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