Potassium Sodium Tartrate → HCID 9982838、化合物

HRID 2371424ノート

反応式

HRID 2371424 の反応式
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][N:8]([CH2:28][CH2:29][O:30][CH3:31])[C:9](=O)[CH2:10][CH:11]1[S:16](=[O:18])(=[O:17])[C:15]2[S:19][C:20]([S:22](=[O:25])(=[O:24])[NH2:23])=[CH:21][C:14]=2[NH:13][C:12]1=[O:26].[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(COC)OC>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][N:8]([CH2:9][CH2:10][CH:11]1[S:16](=[O:18])(=[O:17])[C:15]2[S:19][C:20]([S:22](=[O:24])(=[O:25])[NH2:23])=[CH:21][C:14]=2[NH:13][C:12]1=[O:26])[CH2:28][CH2:29][O:30][CH3:31]

参加物

5

反応物 3

HCID 9357Potassium Sodium TartrateHCID 10255391HCID 10255391、化合物HCID 21226445Aluminium lithium hydride

生成物 1

HCID 9982838HCID 9982838、化合物

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

A solution of N-methoxyethoxyethyl-N-methoxyethyl (2,3-dihydro-2,4,4-trioxo-6-sulfamoyl-1H-thieno[2,3-b][1,4]thiazin-3-yl)acetamide (500 mg, 1 mmol) in dimethoxyethane (5 ml) was added dropwise to a suspension of lithium aluminum hydride (152 mg, 4 mmol) in dimethoxyethane (5 ml) at such a rate that the mixture refluxed gently. When addition was complete, the reaction mixture was refluxed an additional 2 hours. The mixture was cooled in an ice bath and a saturated solution of Rochelle salt was added. The resulting mixture was stirred overnight at ambient temperature, filtered to remove some granular solid, and concentrated to dryness under vacuum. The residue was partitioned between ethyl acetate and 0.5N HCl. The acid fraction was brought to pH 8 by the addition of NH4OH and extracted with ethyl acetate. This ethyl acetate extract was washed with brine and dried over sodium sulfate. After filtration and evaporation of solvent the residue was chromatographed over silica gel eluting with CHCl3 /MeOH/NH4OH (70:30:3) to give 3-[ 2-(N-methoxyethoxyethyl-N-methoxyethylamino)ethyl]-2,3-dihydro-2,4,4-trioxo-6-sulfamoyl-1H-thieno[2,3-b][1,4]thiazine. The free base was converted to the hydrochloride salt hydrate from ethanolic hydrogen chloride and ether, mp 170°-175° C.

後処理

  1. temperaturerefluxed gently
  2. additionWhen addition
  3. temperaturethe reaction mixture was refluxed an additional 2 hours
  4. temperatureThe mixture was cooled in an ice bath
  5. filtrationfiltered
  6. customto remove some granular solid
  7. concentrationconcentrated to dryness under vacuum
  8. customThe residue was partitioned between ethyl acetate and 0.5N HCl
  9. additionThe acid fraction was brought to pH 8 by the addition of NH4OH
  10. extractionextracted with ethyl acetate
  11. extractionThis ethyl acetate extract
  12. washwas washed with brine
  13. dry with materialdried over sodium sulfate
  14. filtrationAfter filtration and evaporation of solvent the residue
  15. customwas chromatographed over silica gel eluting with CHCl3 /MeOH/NH4OH (70:30:3)

出典と根拠

ORDレコード
ord-8f14df301a864dd386f225c48b96b1bc
出典データセット
uspto-grants-1992_03
特許番号
US05093332

反応ノート

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