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

HRID 1417620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1417620
CN(C1C=CC=CN=1)C.[C:10]1([N:16]=[C:17]=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[NH2:19][C@@H:20]1[C:56]([CH3:58])([CH3:57])[C@H:55]2[C@@:23]3([O:51][C:27]4[C:28]5[CH2:29][N:30]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C:31](=[O:43])[C:32]=5[CH:33]=[C:34]([O:35][CH2:36][C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)[C:26]=4[CH2:25][C@:24]3([CH3:60])[C@@H:52]([CH3:59])[CH2:53][CH2:54]2)[CH2:22][CH2:21]1>C1COCC1>[CH2:36]([O:35][C:34]1[C:26]2[CH2:25][C@:24]3([CH3:60])[C@@H:52]([CH3:59])[CH2:53][CH2:54][C@H:55]4[C:56]([CH3:58])([CH3:57])[C@@H:20]([NH:19][C:17]([NH:16][C:10]5[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=5)=[O:18])[CH2:21][CH2:22][C@@:23]34[O:51][C:27]=2[C:28]2[CH2:29][N:30]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C:31](=[O:43])[C:32]=2[CH:33]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Komponenten

5

Edukt 3

HCID 7672Phenyl isocyanateHCID 218852-DimethylaminopyridineHCID 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]isoindole

Produkt 1

HCID 86753822(6aR,7S,9aS,11S,13aS)-5-benzyloxy-2-(t-butoxycarbonyl)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-11-(3-phenylureido)-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindoleAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under nitrogen, 2 mg (0.017 mmol) of dimethylaminopyridine and 12 μl (0.11 mmol) of phenyl isocyanate were added to a solution of Compound (45a) (50 mg, 0.087 mmol) in 2.0 ml of dry THF, and the mixture stirred at room temperature for 30 min. The reaction mixture was then concentrated under reduced pressure. The residue was purified by a preparative thin layer chromatography (Merck, Kieselgel 60 F254, 0.5 mm; chloroform:methanol=40:1) to give 49 mg (81%) of Compound (45e).

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe residue was purified by a preparative thin layer chromatography (Merck, Kieselgel 60 F254, 0.5 mm; chloroform:methanol=40:1)

Quellen und Nachweise

ORD-Eintrag
ord-bad52019976f4ff9b1f9264167ffd00c
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05876984

Notizen zur Reaktion

Wird geladen…