Dimethylformamide → (R)-9-[2-(N-Boc-L-valyloxymethyl)4-(stearoyloxy)butyl]guanine

HRID 48559

Reaktionsgleichung

Reaktionsgleichung von HRID 48559
[C:1]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1(N=C=NC2CCCCC2)CCCCC1.O[CH2:32][C@H:33]([CH2:46][CH2:47][O:48][C:49](=[O:67])[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])[CH2:34][N:35]1[CH:43]=[N:42][C:41]2[C:40](=[O:44])[NH:39][C:38]([NH2:45])=[N:37][C:36]1=2.CN(C)C=O>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([NH:8][C@H:9]([C:13]([O:15][CH2:32][C@H:33]([CH2:46][CH2:47][O:48][C:49](=[O:67])[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])[CH2:34][N:35]1[CH:43]=[N:42][C:41]2[C:40](=[O:44])[NH:39][C:38]([NH2:45])=[N:37][C:36]1=2)=[O:14])[CH:10]([CH3:11])[CH3:12])([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 83693Boc-L-ValineHCID 136343267(R)-9-[2-Hydroxymethyl-4-(stearoyloxy)butyl]guanine

Produkt 1

HCID 135829460(R)-9-[2-(N-Boc-L-valyloxymethyl)4-(stearoyloxy)butyl]guanineAusbeute 39,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of N-Boc-L-valine (528 mg; 2.1 mmol) and N,N′-dicyclohexyl carbodiimide (250 mg; 1.21 mg) in dichloromethane (20 ml) was stirred over night at room temperature, dicyclohexylurea filtered off and extracted with a small volume of dichloromethane, and the filtrate evaporated in vacuo to a small volume. (R)-9-[2-Hydroxymethyl-4-(stearoyloxy)butyl]guanine (340 mg; 0.654 mmol), 4-dimethylaminopyridine (25 mg; 0.205 mmol), and dry N,N-dimethylformamide (15 ml) were added and the mixture was stirred for 4 h at 50° C. under N2. The solvent was evaporated in vacuo to a small volume. Column chromatography on silica gel, then on aluminum oxide (ethyl acetate:methanol: water 15:2:1 as eluent) gave 185 mg (39%) pure title compound as a white solid.

Aufarbeitung

  1. filtrationdicyclohexylurea filtered off
  2. extractionextracted with a small volume of dichloromethane
  3. customthe filtrate evaporated in vacuo to a small volume
  4. stirringthe mixture was stirred for 4 h at 50° C. under N2
  5. customThe solvent was evaporated in vacuo to a small volume

Quellen und Nachweise

ORD-Eintrag
ord-fd5c64ed8b2a4ec8b5c23cabdd62366f
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703394B2

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