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 1417620ノート

反応式

HRID 1417620 の反応式
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

参加物

5

反応物 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

生成物 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]isoindole収率 81.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-bad52019976f4ff9b1f9264167ffd00c
出典データセット
uspto-grants-1999_03
特許番号
US05876984

反応ノート

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