Ethanol → 2'-Deoxy-5'-O-(triphenylmethyl)uridine

HRID 2372518Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2'-deoxyuridine (100 g, 0.44 mol) and triphenylmethyl choride (147 g, 0.53 mol) in 250 mL of pyridine was heated at 100° C. for 30 minutes. One-third of the cooled solution was added at a slow flow rate to a mixture of ice water (2:3) in a commercial blender blending for 3-5 minutes after adding the solution. The resulting white precipitate was filtered and washed twice, stirring in 2 L of water. Recrystallization was accomplished by refluxing the product in a benzene-acetone solution (1:1) for 15 minutes, yielding 128 g (62%). The compound softened at 76° C., began to melt at 152-155° C., and darkened in color at 155-159° C. Rf =0.71 (CHCl3 --EtOH, 4:1).

Workup

additionafter adding the solution
filtrationThe resulting white precipitate was filtered
washwashed twice
customRecrystallization
temperatureby refluxing the product in a benzene-acetone solution (1:1) for 15 minutes
customyielding 128 g (62%)
customsoftened at 76° C.
customto melt at 152-155° C.
customdarkened in color at 155-159° C

Sources & evidence

ORD record: ord-e3adfdbf17394f1dabdb0c81f036d3e0
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05099010

Reaction notes

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