Benzylamine → 2'-Deoxy-N-(phenylmethyl)cytidine

HRID 611464

Reaktionsgleichung

Reaktionsgleichung von HRID 611464
Cl.[C@@H:2]1([N:10]2[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[CH2:3]1.[CH2:18](N)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([NH:15][C:14]1[CH:16]=[CH:17][N:10]([C@@H:2]2[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[CH2:3]2)[C:11](=[O:12])[N:13]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

3

Edukt 2

HCID 7504BenzylamineHCID 107488Deoxycytidine hydrochloride

Produkt 1

HCID 114725832'-Deoxy-N-(phenylmethyl)cytidine

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To 2'-deoxycytidine hydrochloride (5.28g, 20 mmol, U.S. Biochemical Corp., Cleveland, Ohio) was added benzylamine (20 ml), and the mixture was heated at 150° C. for 3 hours under an argon atmosphere. The solution was concentrated under vacuum to yield a viscous yellow oil, which was partitioned between water (100 ml) and ethyl acetate (100 ml). The aqueous phase was washed with ethyl acetate (100 ml) and separated. The aqueous phase was concentrated under vacuum to yield a yellow syrup (13 g), which was purified by silica gel column chromatography with 15:1 methylene chloride:methanol as eluant, to yield the desired product (5.8 g, 91.5%), as a colorless syrup.

Aufarbeitung

  1. concentrationThe solution was concentrated under vacuum
  2. customto yield a viscous yellow oil, which
  3. customwas partitioned between water (100 ml) and ethyl acetate (100 ml)
  4. washThe aqueous phase was washed with ethyl acetate (100 ml)
  5. customseparated
  6. concentrationThe aqueous phase was concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b8d3db90d1494a97b3a91288e18195a4
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06001611

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