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 1417620Notes

Reaction equation

HRID 1417620 reaction equation
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

Participants

5

Reactant 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

Product 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]isoindoleYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-bad52019976f4ff9b1f9264167ffd00c
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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