Trimethylsilylacetylene → (R)-5-Ethynyl-4-[2-(4-heptyloxy-phenyl)-ethyl]-4-methyl-oxazolidin-2-one

HRID 2076795

反応式

HRID 2076795 の反応式
[CH3:1][Si](C#C)(C)C.C([Li])CCC.[C:12]([O:16][C:17](=[O:39])[NH:18][C@:19]([CH:37]=O)(C)[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:24][CH:23]=1)([CH3:15])(C)C>C1COCC1>[C:15]([CH:12]1[O:16][C:17](=[O:39])[NH:18][C@@:19]1([CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:26][CH:27]=1)[CH3:37])#[CH:1]

参加物

5

反応物 3

HCID 66111TrimethylsilylacetyleneHCID 59339517[(R)-1-Formyl-3-(4-heptyloxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl esterHCID 178418339Butyllithium

生成物 1

HCID 86615288(R)-5-Ethynyl-4-[2-(4-heptyloxy-phenyl)-ethyl]-4-methyl-oxazolidin-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a stirred solution of trimethylsilylacetylene (0.18 ml, 1.27 mMol) in THF (18 ml) at −78° C. is added n-Butyllithium (0.49 ml, 2.5 M in cyclohexane). After 5 minutes, [(R)-1-Formyl-3-(4-heptyloxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester (200 mg, 0.51 mMol) in THF (2 ml) is added and the reaction is stirred at −78° C. for 5 hours. After that time, the cooling is removed and the reaction is stirred for 16 hours at RT. The reaction mixture is then poured onto a biphasic mixture of AcOEt and NaHCO3 (saturated aqueous solution). The aqueous phase is extracted with AcOEt (3 times). The combined organic layers are dried (Na2SO4) and concentrated under reduced pressure. Column chromatography eluting with 8%-45% AcOEt in heptane gives (R)-5-Ethynyl-4-[2-(4-heptyloxy-phenyl)-ethyl]-4-methyl-oxazolidin-2-one and its C5 epimer.

後処理

  1. customAfter that time, the cooling is removed
  2. stirringthe reaction is stirred for 16 hours at RT
  3. additionThe reaction mixture is then poured onto a biphasic mixture of AcOEt and NaHCO3 (saturated aqueous solution)
  4. extractionThe aqueous phase is extracted with AcOEt (3 times)
  5. dry with materialThe combined organic layers are dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. washColumn chromatography eluting with 8%-45% AcOEt in heptane

出典と根拠

ORDレコード
ord-a1d21d4534b24d32af958e1968bffb56
出典データセット
uspto-grants-2011_04
特許番号
US07928093B2

関連ノート

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