Acetic Anhydride → HCID 15024562, compound
Reaction equation
Br[C:2]1[N:3]([C:12]2[N:13]=[CH:14][N:15]=[C:16]([NH2:19])[C:17]=2[N:18]=1)[C@@H:4]1[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[CH2:5]1.[C:20]([O-])(=[O:22])[CH3:21].[Na+].C(OC(=O)C)(=[O:27])C>N.N1C=CC=CC=1>[C:20]([NH:19][C:16]1[C:17]2[NH:18][C:2](=[O:27])[N:3]([C:12]=2[N:13]=[CH:14][N:15]=1)[C@@H:4]1[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[CH2:5]1)(=[O:22])[CH3:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
8-Bromo-2′-deoxyadenosine (4.2 g, 12.5 mmol) prepared in above was dissolved in 80% acetic acid-acetic anhydride (1:1, v/v, 250 mL), and sodium acetate (18.5 g, 225 mmol) was added thereto. The mixture was stirred at 120° C. for 3 hours and then extracted with ethyl acetate-water (500 mL/500 mL). The organic layers were combined, and the solvent was removed under reduced pressure. The obtained crude product was dissolved in 28% aqueous ammonia-pyridine (1:1, v/v, 250 mL). The solution was stirred at room temperature for 5 hours. Then, the reaction solvent was evaporated under reduced pressure. The resulting solid was sufficiently washed with ethanol and filtered to give 2′-deoxy-7,8-dihydro-6-N-acetyladenosin-8-one (1.9 g, yield: 55%).
Workup
- extractionextracted with ethyl acetate-water (500 mL/500 mL)
- customthe solvent was removed under reduced pressure
- customThe obtained crude product
- stirringThe solution was stirred at room temperature for 5 hours
- customThen, the reaction solvent was evaporated under reduced pressure
- washThe resulting solid was sufficiently washed with ethanol
- filtrationfiltered
Sources & evidence
- ORD record
- ord-fc7df67c47634dba8c43254e695c8a38
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851157B1
Reaction notes
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