Morpholine → 2-(3-Methoxypropyl)-3-(4-morpholinylmethyl)-2H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide

HRID 1736010ノート

反応式

HRID 1736010 の反応式
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11]([CH2:12]O)=[CH:10][C:9]2[CH:14]=[CH:15][S:16][C:8]=2[S:7]1(=[O:18])=[O:17].C(N(CC)CC)C.CS(OS(C)(=O)=O)(=O)=O.[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11]([CH2:12][N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)=[CH:10][C:9]2[CH:14]=[CH:15][S:16][C:8]=2[S:7]1(=[O:18])=[O:17]

参加物

6

反応物 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 194341212-(3-Methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-3-methanol 1,1-dioxide

生成物 1

HCID 194341012-(3-Methoxypropyl)-3-(4-morpholinylmethyl)-2H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide収率 94%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of the product from Step C (1.30 g, 4.50 mmol) and triethylamine (1.36 g, 13.5 mmol) in anhydrous THF (30 mL) at ambient temperature was added methanesulfonic anhydride (1.18 g, 6.75 mmol). After stirring for 30 min, morpholine (5 mL) was added; this mixture was stirred at ambient temperature for 18 h and then heated at reflux for 1 h. The volatiles were evaporated and a saturated aqueous solution of sodium bicarbonate (100 mL) was added. The mixture was extracted with ethyl acetate (2×100 mL) and the combined extracts were dried (MgSO4) and evaporated to give a viscous oil which was purified by column chromatography (silica, 30 to 50% ethyl acetate/hexane) to give a viscous oil (1.51 g, 94%).

後処理

  1. stirringthis mixture was stirred at ambient temperature for 18 h
  2. temperatureheated
  3. temperatureat reflux for 1 h
  4. customThe volatiles were evaporated
  5. additiona saturated aqueous solution of sodium bicarbonate (100 mL) was added
  6. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
  7. dry with materialthe combined extracts were dried (MgSO4)
  8. customevaporated
  9. customto give a viscous oil which
  10. customwas purified by column chromatography (silica, 30 to 50% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-03540382433b40899ddd5ddbe0db2214
出典データセット
uspto-grants-1996_07
特許番号
US05538966

反応ノート

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