Hydrochloric Acid → (5R)-3-[6-(But-3-ynyloxy)hexyl]5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 720824ノート

反応式

HRID 720824 の反応式
[CH3:1][C:2]1([CH3:18])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[NH:14][CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.[H-].[Na+].[CH2:21]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]Br)[CH2:22][C:23]#[CH:24].Cl>CN(C=O)C>[CH2:21]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][N:14]1[CH2:13][C@@H:12]([C:10]2[CH:9]=[CH:8][C:6]3[O:7][C:2]([CH3:18])([CH3:1])[O:3][CH2:4][C:5]=3[CH:11]=2)[O:16][C:15]1=[O:17])[CH2:22][C:23]#[CH:24]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 10933894(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneHCID 113792816-Bromohexylbut-3-ynyl ether

生成物 1

HCID 42625666(5R)-3-[6-(But-3-ynyloxy)hexyl]5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one収率 86.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (10 g) in DMF (100 ml) was added dropwise to a stirred suspension of sodium hydride (60% oil dispersion, 2.33 g) in DMF (50 ml) with stirring under nitrogen and maintaining the internal temperature at 0°. Stirring was continued at 0–5° for 1 h. The mixture was recooled to 0° and a solution of 6-bromohexyl but-3-ynyl ether (14.7 g) in DMF (50 ml) was added over 1 min. The mixture was then stirred at 20–30° for 2 h. 2M HCl (9 ml) was added and the mixture was partitioned between water and diethyl ether. The aqueous layer was extracted with more diethyl ether and the combined organic layers were washed twice with brine. After drying (MgSO4) the solution was concentrated and loaded onto a column of silica gel (600 g) set up in diethyl ether: petroleum ether (bp 40–60°) (1:2). The column was eluted successively with this mixture, then (1:1) and then diethyl ether to give the title compound (13.88 g) LCMS RT=3.45 min.

後処理

  1. temperaturemaintaining the internal temperature at 0°
  2. stirringStirring
  3. customwas recooled to 0°
  4. stirringThe mixture was then stirred at 20–30° for 2 h
  5. customthe mixture was partitioned between water and diethyl ether
  6. extractionThe aqueous layer was extracted with more diethyl ether
  7. washthe combined organic layers were washed twice with brine
  8. dry with materialAfter drying (MgSO4) the solution
  9. concentrationwas concentrated
  10. washThe column was eluted successively with this mixture

出典と根拠

ORDレコード
ord-aa1ac8e525de49c7a1654a2f03ff6399
出典データセット
uspto-grants-2006_11
特許番号
US07135600B2

反応ノート

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