Ethanol → 3'-O-Methanesulfonyl-5'-O-trityl-2'-deoxyuridine

HRID 2372519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2372519
[C:1]([O:20][CH2:21][C@H:22]1[O:26][C@@H:25]([N:27]2[CH:34]=[CH:33][C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:24][C@@H:23]1[OH:35])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:36][S:37](Cl)(=[O:39])=[O:38].C(Cl)(Cl)Cl.CCO>N1C=CC=CC=1>[CH3:36][S:37]([O:35][C@@H:23]1[C@@H:22]([CH2:21][O:20][C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:26][C@@H:25]([N:27]2[CH:34]=[CH:33][C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:24]1)(=[O:39])=[O:38]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 6212ChloroformHCID 31297Methanesulfonyl chlorideHCID 137119602'-Deoxy-5'-O-(triphenylmethyl)uridine

Produkt 1

HCID 137119623'-O-Methanesulfonyl-5'-O-trityl-2'-deoxyuridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
4 °C

Versuchsvorschrift

The product of Example 1 (59 g, 0.13 mol) was dissolved at room temperature in 120 mL of pyridine. The solution was put into an ice bath and 29 mL of methanesulfonyl chloride (0.34 mol) was added dropwise. The resulting solution was allowed to stir at 4° C. for 24 hours. The reaction mixture was added in three portions at a slow flow rate into a blender as described previously. The pea-green solid was collected by filtration, washed twice with 2 L of water, and dried to yield 58 g (93%). The compound started to soften at 85° C. and melted at 106-108° C. Rf =0.62 (CHCl3 --EtOH, 10:1). Anal. (C29H28N2O7S).

Aufarbeitung

  1. customThe solution was put into an ice bath
  2. additionThe reaction mixture was added in three portions at a slow flow rate into a blender
  3. filtrationThe pea-green solid was collected by filtration
  4. washwashed twice with 2 L of water
  5. customdried
  6. customto yield 58 g (93%)
  7. customto soften at 85° C.

Quellen und Nachweise

ORD-Eintrag
ord-3ebd16bc27884e7cb445390ed9808b90
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05099010

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