Nitric Acid → HCID 86608921, compound
Reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:24][C@H:23]([CH2:25][O:26][C:27](=[O:29])[CH3:28])[C@@H:17]([O:18][C:19](=[O:22])[CH2:20][CH3:21])[C@H:12]3[O:13][C:14](=[O:16])[CH3:15])[C:4]=2[N:5]=[CH:6][N:7]=1.[N+:30]([O-])([OH:32])=[O:31].OS(O)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]2[C:10]([N+:30]([O-:32])=[O:31])=[CH:9][N:8]([C@@H:11]3[O:24][C@H:23]([CH2:25][O:26][C:27](=[O:29])[CH3:28])[C@@H:17]([O:18][C:19](=[O:22])[CH2:20][CH3:21])[C@H:12]3[O:13][C:14](=[O:16])[CH3:15])[C:4]=2[N:5]=[CH:6][N:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of the product from Step 2 (700 mg, 1.64 mmol) in DCM was cooled to 0° C. in ice/water bath. Meanwhile fuming HNO3 (1 mL) and H2SO4 (1 mL) were premixed and added dropwise to a vigorously stirred DCM solution containing the protected nucleoside and the mixture. The solution was stirred at 0° C. for 1.5 hours then quenched by pouring into an ice cold saturated Na2CO3 solution (125 mL). The product was extracted with DCM and the organic layers were dried over Na2SO4 and concentrated in vacuo. The crude purified by Isco CombiFlash purification system with a 40 g silica gel column and 0-35% MeOH gradient in DCM over 30 minutes to afford 440 mg (52%).
Workup
- customthen quenched
- additionby pouring into an ice cold saturated Na2CO3 solution (125 mL)
- extractionThe product was extracted with DCM
- dry with materialthe organic layers were dried over Na2SO4
- concentrationconcentrated in vacuo
- customThe crude purified by Isco CombiFlash purification system with a 40 g silica gel column and 0-35% MeOH gradient in DCM over 30 minutes
- customto afford 440 mg (52%)
Sources & evidence
- ORD record
- ord-1013ce5fd9384dcd9ab40b1fa17ad9c7
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07524825B2
Reaction notes
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