Hydrochloric Acid → Tert-butyl 4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide

HRID 1521712ノート

反応式

HRID 1521712 の反応式
[CH3:1][CH:2]1[CH:6]([CH3:7])[O:5][S:4](=[O:8])[N:3]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].I([O-])(=O)(=O)=[O:17].[Na+].Cl>C(#N)C.O>[CH3:1][CH:2]1[CH:6]([CH3:7])[O:5][S:4](=[O:17])(=[O:8])[N:3]1[C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 23667635Sodium periodateHCID 67234977Tert-butyl 4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2-oxide

生成物 1

HCID 86682386Tert-butyl 4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide収率 89.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒3 回HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

tert-Butyl 4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2-oxide (4.7 g, 20.0 mmol) is dissolved in acetonitrile (50 mL) and H2O (30 mL) is added. The reaction mixture is cooled to 0° C. and sodium periodate (6.4 g, 30.0 mmol) is added. After 5 min, the pH of the mixture is adjusted to 7-8 by addition of saturated Na2HPO4 solution. Then the solution of RuCl3 (42 mg, 0.2 mmol) in H2O (0.5 mL) is added. The pH of the reaction mixture is kept between 6 and 9 by addition of Na2HPO4 solution. After stirring for 2 h, H2O (100 mL) is added and the pH is adjusted to 6 by addition of 2M HCl solution. The mixture is extracted with EtOAc and the organic layer is separated, washed with NaHCO3 and brine. The aqueous layers are back extracted once with EtOAc. Then all organic layers are combined, dried (MgSO4) and concentrated. Purification by flash column chromatography using a gradient elution of 5-80% ethyl acetate/hexanes affords the title compound (4.48 g, 89%).

後処理

  1. extractionThe mixture is extracted with EtOAc
  2. customthe organic layer is separated
  3. washwashed with NaHCO3 and brine
  4. extractionThe aqueous layers are back extracted once with EtOAc
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by flash column chromatography
  8. washa gradient elution of 5-80% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-5a054b46e1de445ab52707ba1827944a
出典データセット
uspto-grants-2015_07
特許番号
US09073926B2

反応ノート

読み込み中…