Water → (6aR,7S,9aS,11S,13aS)-11-amino-5-benzyloxy-2-(t-butoxycarbonyl)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

HRID 1417616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1417616
[N:1]([C@@H:4]1[C:40]([CH3:42])([CH3:41])[C@H:39]2[C@@:7]3([O:35][C:11]4[C:12]5[CH2:13][N:14]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:15](=[O:27])[C:16]=5[CH:17]=[C:18]([O:19][CH2:20][C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[C:10]=4[CH2:9][C@:8]3([CH3:44])[C@@H:36]([CH3:43])[CH2:37][CH2:38]2)[CH2:6][CH2:5]1)=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>C1COCC1>[NH2:1][C@@H:4]1[C:40]([CH3:42])([CH3:41])[C@H:39]2[C@@:7]3([O:35][C:11]4[C:12]5[CH2:13][N:14]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:15](=[O:27])[C:16]=5[CH:17]=[C:18]([O:19][CH2:20][C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[C:10]=4[CH2:9][C@:8]3([CH3:44])[C@@H:36]([CH3:43])[CH2:37][CH2:38]2)[CH2:6][CH2:5]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 86753815(6aR,7S,9aS,11S,13aS)-11-azido-5-benzyloxy-2-(t-butoxycarbonyl)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

Produkt 1

HCID 86753816(6aR,7S,9aS,11S,13aS)-11-amino-5-benzyloxy-2-(t-butoxycarbonyl)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindoleAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To the above Compound (44) (300 mg, 0.50 mmol) dissolved in 10 ml of THF were added 1.0 ml of water and 270 mg (1.03 mmol) of triphenylphosphine. The mixture was heated to reflux for 24 hours. After the addition of ethyl acetate, it was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was loaded onto a silica gel column (silica gel 20 g), followed by elution with 60 ml of ethyl acetate to remove nonpolar fractions. The polar fractions eluted with 120 ml of ethyl acetate and 80 ml of chloroform-methanol (20:1) mixture were combined, and concentrated under reduced pressure. The residue was further purified by a column chromatography (Merck, Lobar column, size B; chloroform:methanol=20:1-10:1) to give 262 mg (83%) of Compound (45a) as a powdery material.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24 hours
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washfollowed by elution with 60 ml of ethyl acetate
  6. customto remove nonpolar fractions
  7. washThe polar fractions eluted with 120 ml of ethyl acetate and 80 ml of chloroform-methanol (20:1) mixture
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was further purified by a column chromatography (Merck, Lobar column, size B; chloroform:methanol=20:1-10:1)

Quellen und Nachweise

ORD-Eintrag
ord-6c60654c894d4a4e80e22b961e4aa841
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05876984

Notizen zur Reaktion

Wird geladen…