1,3-Propanediamine, N1,N1,N3-trimethyl- → (1E,4S,4aR,5R,6aS,7S)-1-{[[3-(dimethylamino)propyl](methyl)amino]methylene}-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 1445980

Reaktionsgleichung

Reaktionsgleichung von HRID 1445980
[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].[CH3:32][N:33]([CH3:39])[CH2:34][CH2:35][CH2:36][NH:37][CH3:38]>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]\[N:37]([CH2:36][CH2:35][CH2:34][N:33]([CH3:39])[CH3:32])[CH3:38])/[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[CH: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 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 986734017beta-Hydroxy wortmannin

Produkt 1

HCID 11599195(1E,4S,4aR,5R,6aS,7S)-1-{[[3-(dimethylamino)propyl](methyl)amino]methylene}-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 36,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 50 mg (0.12 mmol) 17-hydroxywortmannin in 0.5 mL CH2Cl2 is added 27.9 mg (0.24 mmol) N,N,N′-trimethyl-1,3-propanediamine. The reaction mixture is stirred at room temperature overnight. CH2Cl2 is removed in vacuo. The residue is triturated with Et2O to give 24 mg (36.6%) product as an orange powder. MS (ESI) m/z 547.3 (M+1).

Aufarbeitung

  1. customCH2Cl2 is removed in vacuo
  2. customThe residue is triturated with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-3fbc0786560c4d0fb841fa8e206c2d6d
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666901B2

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