Water → N2 (4-methoxyphenyldiphenylmethyl)-9-(1,3-din-octanoyloxy-2-propoxymethyl)guanine

HRID 1381762

Reaktionsgleichung

Reaktionsgleichung von HRID 1381762
[N:1]#[N:2].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([NH:24][C:25]2[NH:26][C:27](=[O:41])[C:28]3[N:29]=[CH:30][N:31]([CH2:34][O:35][CH:36]([CH2:39][OH:40])[CH2:37][OH:38])[C:32]=3[N:33]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1.[C:42](Cl)(=[O:50])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49].[OH2:52]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.C(Cl)Cl>[N:1]#[N:2].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([NH:24][C:25]2[NH:26][C:27](=[O:41])[C:28]3[N:29]=[CH:30][N:31]([CH2:34][O:35][CH:36]([CH2:37][O:38][C:9](=[O:52])[CH2:10][CH2:5][CH2:6][CH2:7][CH2:8][CH2:11][CH3:12])[CH2:39][O:40][C:42](=[O:50])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[C:32]=3[N:33]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:9][CH:10]=1

Komponenten

7

Edukt 3

HCID 962WaterHCID 8124Octanoyl chlorideHCID 136387272N2 (4-methoxyphenyldiphenylmethyl)-9-(1,3-dihydroxy-2-propoxymethyl)guanine

Produkt 1

HCID 136332157N2 (4-methoxyphenyldiphenylmethyl)-9-(1,3-din-octanoyloxy-2-propoxymethyl)guanine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a magnetically stirred solution of 1.05 g of N2 -(4-methoxyphenyldiphenylmethyl)-9-(1,3-dihydroxy-2-propoxymethyl)guanine and 25 mg of 4-dimethylaminopyridine in 30 ml of dry pyridine was added dropwise a solution of 1.2 g of n-octanoyl chloride in 10 ml of methylene chloride. After 15 hour, 1.5 ml of water was added and the solution concentrated at reduced pressure. The residue was chromatographed over silica gel eluting with 1:9 methanol:methylene chloride to give a white solid which was recrystallized from ethyl acetate:hexane to N2 -(4-methoxyphenyldiphenylmethyl)-9-(1,3-di-n-octanoyloxy-2-propoxymethyl)guanine.

Aufarbeitung

  1. concentrationthe solution concentrated at reduced pressure
  2. customThe residue was chromatographed over silica gel eluting with 1:9 methanol
  3. custommethylene chloride to give a white solid which
  4. customwas recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d8315da918c841329a0559a8b51e8318
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04803271

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