Trityl chloride → 2'-Deoxy-5'-O-(triphenylmethyl)uridine
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>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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
2′-deoxyuridine (4.00 g, 17.5 mmol) and triphenylmethyl chloride (5.37 g, 19.25 mmol) were stirred in anhydrous pyridine (70 ml) at 50° C. overnight. Additional triphenylmethyl chloride (1.00 g, 3.59 mmol) was added after 18 hours, and the mixture was stirred for a further 4 hours at 50° C. The reaction mixture was then poured into ice-H2O (300 ml) and stirred vigorously. The precipitate was extracted with EtOAc (3×100 ml). The organic solution was then washed with 0.5 M HCl (4×100 ml), dried with MgSO4 and filtered. The filtrate was then washed further with EtOAc, which was then evaporated, and finally with DCM. Solvent was removed using a Buchi rotary evaporator, and finally with the vacuum pump.
Workup
- stirringstirred vigorously
- extractionThe precipitate was extracted with EtOAc (3×100 ml)
- washThe organic solution was then washed with 0.5 M HCl (4×100 ml)
- dry with materialdried with MgSO4
- filtrationfiltered
- washThe filtrate was then washed further with EtOAc, which
- customwas then evaporated
- customSolvent was removed
- customa Buchi rotary evaporator
Sources & evidence
- ORD record
- ord-27c6c99c52a94762a9fca55afb04c59b
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07601702B2
Reaction notes
Loading…