Potassium Carbonate → (S)-N-{3-[4-(4-(Prop-2-yn-1-yl)-4-hydroxypiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

HRID 1026670ノート

反応式

HRID 1026670 の反応式
[Li][C:2]#[C:3][Si](C)(C)C.[O:8]=[C:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][C@H:24]([CH2:26][NH:27][C:28](=[O:30])[CH3:29])[O:23][C:22]3=[O:31])=[CH:17][C:16]=2[F:32])[CH2:11][CH2:10]1.[Cl-].[NH4+].[C:35](=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH2:35]([C:9]1([OH:8])[CH2:10][CH2:11][N:12]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][C@H:24]([CH2:26][NH:27][C:28](=[O:30])[CH3:29])[O:23][C:22]3=[O:31])=[CH:17][C:16]=2[F:32])[CH2:13][CH2:14]1)[C:2]#[CH:3]

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 54375226N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamideHCID 178506808HCID 178506808、化合物

生成物 1

HCID 11749595(S)-N-{3-[4-(4-(Prop-2-yn-1-yl)-4-hydroxypiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide収率 19%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
78 °C

実験手順

A mixture of lithio(trimethylsilyl)acetylene (1.72 mmol) and (S)—N-{3-[4-(4-oxo-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (1.72 mmol) in tetrahydrofuran (10 ml) was stirred at a temperature—78° C. for 15 minutes. It was allowed to come to room temperature and further stirred for 18 hours. The reaction mixture was then stirred with aqueous solution of ammonium chloride, the reaction mixture was extracted with ethyl acetate (3×40 ml). The removal of the solvent provided a residue, which was stirred in aqueous methanolic (15 ml) solution of potassium carbonate (1.72 mmol) for 3 hours. The solvent was removed and the residual mass was purified by column chromatography over silica gel to provide title compound in 19% yield. M.P. 166-167° C. and MS (M+1)=376 (MH+, 100%) M.F.=C19H22FN3O4.

後処理

  1. customto come to room temperature
  2. stirringfurther stirred for 18 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate (3×40 ml)
  4. customThe removal of the solvent
  5. customprovided a residue, which
  6. customThe solvent was removed
  7. customthe residual mass was purified by column chromatography over silica gel

出典と根拠

ORDレコード
ord-247f63c77a014233bbc7514c526ed5ec
出典データセット
uspto-grants-2014_05
特許番号
US08729269B2

反応ノート

読み込み中…