1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (5R)-((3S,3aR,6S,6aR)-6-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-yl) 5,6-bis(nitrooxy)hexanoate

HRID 1676009ノート

反応式

HRID 1676009 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH:12]2[O:13][CH2:14][CH:15]([OH:16])[CH:11]2[O:10][CH2:9]1.[N+:17]([O:20][C@@H:21]([CH2:37][O:38][N+:39]([O-:41])=[O:40])[CH2:22][CH2:23][CH2:24][C:25](O[C@@H]1CO[C@@H]2[C@H](O)CO[C@H]12)=[O:26])([O-:19])=[O:18].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[N+:17]([O:20][C@@H:21]([CH2:37][O:38][N+:39]([O-:41])=[O:40])[CH2:22][CH2:23][CH2:24][C:25]([O:16][C@H:15]1[CH2:14][O:13][C@@H:12]2[C@@H:8]([O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)[CH2:9][O:10][C@H:11]12)=[O:26])([O-:19])=[O:18]

参加物

6

反応物 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 58209361(R)-((3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl) 5,6-bis(nitrooxy)hexanoateHCID 767032036-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol

生成物 1

HCID 58209453(5R)-((3S,3aR,6S,6aR)-6-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-yl) 5,6-bis(nitrooxy)hexanoate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

3S,3aR,6S,6aR)-6-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol (0.64 g, 2.80 mmol) and (5R)-5,6-bis-nitrooxy-hexanoic acid (1.18 g, 4.95 mmol) (obtained as described in EXAMPLE 5) were dissolved in DCM (30 ml), EDAC (0.81 g, 4.20 mmol) and 4-dimethylaminopyridine (0.068 g, 0.56 mmol) were added. After stirring at room temperature for 12 hrs, the reaction mixture was washed with water. The organic layer was dried over sodium sulfate, and evaporated under reduced pressure. The residue was purified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 10 to 80%), affording the title product as an oil.

後処理

  1. washthe reaction mixture was washed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 10 to 80%)

出典と根拠

ORDレコード
ord-8ec63b848ddc4352a727f38c2359e52e
出典データセット
uspto-grants-2011_08
特許番号
US08003811B2

反応ノート

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