Hydroxyamine hydrochloride → Thymine
Reaction equation
[Si](O[C@@H]1[C@@](C=O)(CO)O[C@@H]([N:18]2[CH:26]=[C:24]([CH3:25])[C:22](=[O:23])[NH:21][C:19]2=[O:20])C1)(C(C)(C)C)(C)C.NO.Cl>N1C=CC=CC=1>[NH:18]1[CH:26]=[C:24]([CH3:25])[C:22](=[O:23])[NH:21][C:19]1=[O:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 24 °C
Procedure
A solution of the 4'-α and 4'-β isomers 3'-O-t-butyldimethylsilyl-4'-formylthymidine (380 mg, 1 mM), the compound of Formula 12, prepared, e.g., as described in Preparation 8, with H2NOH HCl (110 mg, 1.6 mM) in pyridine (1.5 ml) was stirred at 24° C. for 16 hours. The solvent was removed by evaporation. The residue was partitioned between H2O (5 ml) and EtOAc (15 ml). The aqueous layer was extracted with EtOAc (10 ml), and the EtOAc fractions were combined. The solvent was removed by evaporation and the residue was purified on a thick silica gel plate (60% EtOAc/hexane), 3'-O-t-butyldimethylsilyl-4'-hydroxyiminomethylthymidine (148 mg, 0.37 mM). MS (399 M+).
Workup
- customThe solvent was removed by evaporation
- customThe residue was partitioned between H2O (5 ml) and EtOAc (15 ml)
- extractionThe aqueous layer was extracted with EtOAc (10 ml)
- customThe solvent was removed by evaporation
- customthe residue was purified on a thick silica gel plate (60% EtOAc/hexane), 3'-O-t-butyldimethylsilyl-4'-hydroxyiminomethylthymidine (148 mg, 0.37 mM)
Sources & evidence
- ORD record
- ord-eeff05ee2c0443a0ae7586e840f03be6
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05192749
Reaction notes
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