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 1676009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1676009
[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]

Komponenten

6

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-8ec63b848ddc4352a727f38c2359e52e
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003811B2

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