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 1676009노트

반응식

HRID 1676009 반응식
[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]

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-8ec63b848ddc4352a727f38c2359e52e
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003811B2

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