Aniline → (1E,4S,4aR,5R,6aS,7S,9aR)-1-(anilinomethylene)-7,11-dihydroxy-4-(methoxymethyl)-4a,6a-dimethyl-2,10-dioxo-1,2,4,4a,5,6,6a,7,8,9,9a,10-dodecahydroindeno[4,5-h]isochromen-5-yl acetate

HRID 1445978Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1445978
[CH3:1][C:2]([O:4][C@H:5]1[C:14]2[C@@:15]3([CH3:30])[C@@H:26]([CH2:27][O:28][CH3:29])[O:25][C:23](=[O:24])[C:17]4=[CH:18][O:19][C:20]([C:21](=[O:22])[C:13]=2[C@@H:8]2[CH2:9][CH2:10][C@H:11]([OH:12])[C@@:7]2([CH3:31])[CH2:6]1)=[C:16]34)=[O:3].[NH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(Cl)Cl>[C:2]([O:4][C@H:5]1[C:14]2[C@:15]3([CH3:30])[C:16](/[C:17](=[CH:18]\[NH:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)/[C:23](=[O:24])[O:25][C@@H:26]3[CH2:27][O:28][CH3:29])=[C:20]([OH:19])[C:21](=[O:22])[C:13]=2[C@H:8]2[C@@:7]([CH3:31])([C@@H:11]([OH:12])[CH2:10][CH2:9]2)[CH2:6]1)(=[O:3])[CH3:1]

Komponenten

4

Edukt 2

HCID 6115AnilineHCID 986734017beta-Hydroxy wortmannin

Produkt 1

HCID 68541839(1E,4S,4aR,5R,6aS,7S,9aR)-1-(anilinomethylene)-7,11-dihydroxy-4-(methoxymethyl)-4a,6a-dimethyl-2,10-dioxo-1,2,4,4a,5,6,6a,7,8,9,9a,10-dodecahydroindeno[4,5-h]isochromen-5-yl acetateAusbeute 42,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 50 mg (0.116 mmol) 17-hydroxywortmannin in 1 mL CH2Cl2 is added 26.2 mL (0.287 mmol) aniline. The reaction mixture is stirred at room temperature for 1 week and then concentrated in vacuo. The residue is dissolved in EtOAc and triturated with hexane to give a yellow powder. The yellow powder is purified by silica gel chromatography, (hexane/EtOAc) to give an oil. The oil is triturated with hexane to give 26 mg (42.8%) product as an orange powder. HRMS (ESI) m/z calcd for C29H33NO8 523.22074, found: 524.22692 (M+H)+1.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in EtOAc
  3. customtriturated with hexane
  4. customto give a yellow powder
  5. customThe yellow powder is purified by silica gel chromatography, (hexane/EtOAc)
  6. customto give an oil
  7. customThe oil is triturated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-1369e43a326248f7a90abd5ac51457f1
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666901B2

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