Carbon Dioxide → HCID 9950702, compound
Reaction equation
C([CH:4]=[CH:5][CH:6]=[CH:7][C:8]1[C:9](=[O:23])[NH:10][C:11](=[O:22])[N:12]([CH:21]=1)[C@@H:13]1[O:20][C@H:17]([CH2:18][OH:19])[C@@H:15]([OH:16])[CH2:14]1)(O)=O.[Br:24]N1C(=O)CCC1=O.C(=O)=O>CN(C=O)C>[Br:24]/[CH:4]=[CH:5]\[CH:6]=[CH:7]\[C:8]1[C:9](=[O:23])[NH:10][C:11](=[O:22])[N:12]([CH:21]=1)[C@@H:13]1[O:20][C@H:17]([CH2:18][OH:19])[C@@H:15]([OH:16])[CH2:14]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 5-(4-carboxy-1,3-butadienyl)-2′-deoxyuridine (VI) (0.200 g, 0.62 mmol) in DMF (1 mL) was added KHCO3 (0.185 g, 1.84 mmol) and the mixture was stirred for 20 mm at 25° C. A solution of N-bromosuccinimide (0.117 g, 0.65 mmol) in DMF (0.3 mL) was added dropwise. Smooth gas evolution (CO2) occurred throughout the addition. The resulting brown suspension was stirred for 2 h at 25° C. at which time TLC showed that (VI) was completely consumed. Water (10 mL) was added to the suspension and the resulting solution was extracted with EtOAc (2×15 mL). The extract was dried over MgSO4 and the solvent was evaporated in vacuc to give a yellow solid (178 mg, 80% yield) consisting of a mixture of two isomers as shown by 1H NMR. The crude product was separated by semi-preparative HPLC (reversed phase C18 column) using 20% acetonitrile in water as the mobile phase to give the following isomers:
Workup
- stirringThe resulting brown suspension was stirred for 2 h at 25° C. at which time TLC
- customwas completely consumed
- additionWater (10 mL) was added to the suspension
- extractionthe resulting solution was extracted with EtOAc (2×15 mL)
- dry with materialThe extract was dried over MgSO4
- customthe solvent was evaporated in vacuc
Sources & evidence
- ORD record
- ord-0f226139f23e481ab5d5e9ff263217ef
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07605144B2
Reaction notes
Loading…