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Phosphate → (5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-[6-(4-pentyn-1-yloxy)hexyl]-1,3-oxazolidin-2-one

HRID 2118339
ノート
印刷プレビュー

反応式

HRID 2118339 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:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]Br)[CH2:22][CH2:23][C:24]#[CH:25].P([O-])([O-])([O-])=O>CN(C=O)C.O>[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])[N:14]([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][O:26][CH2:21][CH2:22][CH2:23][C:24]#[CH:25])[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 10933894(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneHCID 218671996-Bromohexyl 4-pentyn-1-yl ether

生成物 1

HCID 86607678(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-[6-(4-pentyn-1-yloxy)hexyl]-1,3-oxazolidin-2-one収率 84%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (Example 1vi) (500 mg) in DMF (15 ml) under nitrogen at 0° was treated with sodium hydride (60% dispersion in mineral oil, 96 mg) and the mixture stirred at 20° for 10 min. A solution of 6-bromohexyl 4-pentyn-1-yl ether (WO 02/066422) (545 mg) in DMF (1 ml) was added and the mixture stirred at 20° for 18 h. Phosphate buffer solution (pH 6.5) and water were added and the mixture was extracted with EtOAc. The extract was washed with water and dried (Na2SO4). Solvent evaporation in vacuo gave a residue, which was purified by flash chromatography on silica gel. Elution with EtOAc-PE (2:3) gave the title compound (700 mg). LCMS RT=3.48 min.

後処理

  1. stirringthe mixture stirred at 20° for 18 h
  2. extractionthe mixture was extracted with EtOAc
  3. washThe extract was washed with water
  4. dry with materialdried (Na2SO4)
  5. customSolvent evaporation in vacuo
  6. customgave a residue, which
  7. customwas purified by flash chromatography on silica gel
  8. washElution with EtOAc-PE (2:3)

出典と根拠

ORDレコード
ord-30bd76360b7e4f5b8f4de3a873c99c96
出典データセット
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07442839B2

反応ノート

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