3,4-Hexanedione → HCID 10159646、化合物

HRID 1167374ノート

反応式

HRID 1167374 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@@H:13]2[O:18][C:17]3[C:19]([NH2:24])=[C:20]([NH2:23])[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:25][CH2:26][C:27](=O)[C:28](=O)[CH2:29][CH3:30]>O.C(O)C.C(=O)([O-])O.[Na+]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]2[O:18][C:17]3=[C:19]4[C:20](=[CH:21][CH:22]=[C:16]3[O:15][CH2:14]2)[N:23]=[C:28]([CH2:29][CH3:30])[C:27]([CH2:26][CH3:25])=[N:24]4)(=[O:10])=[O:9])=[CH:4][CH:3]=1

参加物

6

反応物 2

HCID 625393,4-HexanedioneHCID 11302542HCID 11302542、化合物

生成物 1

HCID 10159646HCID 10159646、化合物

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
60 °C

実験手順

To a solution of [(2R)-7,8-diamino-2,3-dihydro-1,4-benzodioxin-2-yl]-methyl 4-methylbenzenesulfonate (2.226 g, 5.258 mmole) in water (50 mL) was added a solution of 3,4-hexanedione (0.750 g, 6.572 mmole) in ethyl alcohol (50 mL) and the reaction mixture was heated at 60° C. for 3 hours. The reaction mixture was allowed to cool to room temperature and was diluted with aqueous sodium hydrogen carbonate (250 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with water (100 mL), aqueous sodium chloride (100 mL), dried (magnesium sulfate) and the solvent was removed in vacuo to give a crude solid. Purification by flash column chromatography (silica, ethyl acetate:hexanes 7:3) gave 1.796 g (80%) of the (R)-enantiomer of the title compound as a tan crystalline solid. Rf=0.85 (silica, ethyl acetate:hexanes 7:3); mp 132-135° C.

後処理

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washThe combined organic extracts were washed with water (100 mL), aqueous sodium chloride (100 mL)
  4. dry with materialdried (magnesium sulfate)
  5. customthe solvent was removed in vacuo
  6. customto give a crude solid
  7. customPurification by flash column chromatography (silica, ethyl acetate:hexanes 7:3)

出典と根拠

ORDレコード
ord-b8fa5ff0a3594aeeaaead17eedcd41ce
出典データセット
uspto-grants-2003_09
特許番号
US06617327B2

反応ノート

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