5'-Amino-2',5'-dideoxy-5-ethyluridine → 2',5'-dideoxy-5-ethyl-5'-[2(RS)-(2,4-dichlorophenoxy)propylamino]uridine

HRID 1031864

Reaktionsgleichung

Reaktionsgleichung von HRID 1031864
[NH2:1][CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[CH:15]=[C:14]([CH2:16][CH3:17])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:18].C([BH3-])#N.[Na+].[Cl:23][C:24]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:25]=1[O:26][CH:27]([CH3:30])[CH:28]=O>CO.O>[CH2:16]([C:14]1[C:12](=[O:13])[NH:11][C:9](=[O:10])[N:8]([CH:15]=1)[C@@H:6]1[O:7][C@H:3]([CH2:2][NH:1][CH2:30][CH:27]([O:26][C:25]2[CH:31]=[CH:32][C:33]([Cl:35])=[CH:34][C:24]=2[Cl:23])[CH3:28])[C@@H:4]([OH:18])[CH2:5]1)[CH3:17]

Komponenten

6

Edukt 3

HCID 4518285'-Amino-2',5'-dideoxy-5-ethyluridineHCID 5003444Sodium cyanoborohydrideHCID 221663592-(2,4-Dichlorophenoxy)propanal

Produkt 1

HCID 186361762',5'-dideoxy-5-ethyl-5'-[2(RS)-(2,4-dichlorophenoxy)propylamino]uridineAusbeute 32,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution, cooled in ice, of 0.45 g of 5'-amino-2',5'-dideoxy-5-ethyluridine in 28 ml of methanol and 9 ml of water were added 0.17 g of sodium cyanoborohydride followed by 0.5 g of 2-(2,4-dichlorophenoxy)propionaldehyde. The mixture was allowed to warm to room temperature and was then stirred at room temperature for 3 days. The solution was concentrated in order to remove methanol, diluted with 20 ml of water and extracted three times with 15 ml of methylene chloride. The combined extracts were dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using methanol/methylene chloride (1:12) for the elution. There was obtained 0.26 g of 2',5'-dideoxy-5-ethyl-5'-[2(RS)-(2,4-dichlorophenoxy)-propylamino]uridine, mp 51°-61° C.

Aufarbeitung

  1. concentrationThe solution was concentrated in order
  2. customto remove methanol
  3. additiondiluted with 20 ml of water
  4. extractionextracted three times with 15 ml of methylene chloride
  5. dry with materialThe combined extracts were dried over sodium sulphate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. washfor the elution

Quellen und Nachweise

ORD-Eintrag
ord-e642e6b0bb014088b8fa478578be2c08
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04956346

Verknüpfte Notizen

Wird geladen…