Trityl chloride → 2'-Deoxy-5'-O-(triphenylmethyl)uridine

HRID 892419Notes

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](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>N1C=CC=CC=1>[C:17]([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:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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 solution of (50 g, 0.22 mole) of 2'-deoxyuridine and 62 g (0.22 mole) of trityl chloride in 350 ml of dry pyridine was placed in a preheated (100° C.) flask and stirred at 100° C. under air condenser for two hours. The reaction mixture was cooled to room temperature and slowly poured into 4 L of vigorously stirred ice-water. The solid obtained was filtered, washed with water until free from pyridine, and dissolved in chloroform and dried (Na2SO4 or MgSO4). Filtration and evaporation of chloroform yielded the 5'-O-trityl-2'-deoxyuridine product as an syrup (96 g, 93%), which was used for the next reaction without further purification.

Workup

customwas placed in a preheated (100° C.) flask
temperatureThe reaction mixture was cooled to room temperature
customThe solid obtained
filtrationwas filtered
washwashed with water until free from pyridine
dissolutiondissolved in chloroform
dry with materialdried (Na2SO4 or MgSO4)
filtrationFiltration and evaporation of chloroform

Sources & evidence

ORD record: ord-44c184be887f430ca51306c444e7c650
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05118672

Reaction notes

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