Palmitoyl chloride → HCID 69414239, compound
Reaction equation
O.O.[C@@H:3]1([N:12]2[C:22]3[NH:21][C:19](=[O:20])[NH:18][C:16](=[O:17])[C:15]=3[N:14]=[CH:13]2)[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[C@H:4]1[OH:5].[C:23](Cl)(=[O:39])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>CN(C1C=CN=CC=1)C.CN(C)C=O>[C:23]([C@@:3]1([N:12]2[C:22]3[NH:21][C:19](=[O:20])[NH:18][C:16](=[O:17])[C:15]=3[N:14]=[CH:13]2)[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[C@H:4]1[OH:5])(=[O:39])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a 50 mL flask was added xanthosine dihydrate (1.0 g, 3.52 mmol) and N,N-dimethyl-4-aminopyridine (0.0086 g, 0.07 mmol). N,N-dimethylformamide (16 mL) was added via cannula with stirring, the flask was purged with argon gas and pyridine (8 mL) was added via cannula. The slurry was allowed to cool 10 min. in an ice/NaCl bath and palmitoyl chloride (1.6 mL, 9.2 mmol) was added dropwise. The mixture was allowed to stir while it slowly warmed to 25° C. After 18 h, the mixture was poured into 300 mL of ice-cold 0.1 M sodium bicarbonate solution giving a white solid which was isolated by suction filtration, washed with 3×100 mL hot water, air dried, and recrystallized from hot methanol.
Workup
- customthe flask was purged with argon gas and pyridine (8 mL)
- additionwas added via cannula
- temperatureto cool 10 min. in an ice/NaCl bath
- stirringto stir while it
- customgiving a white solid which
- customwas isolated by suction filtration
- washwashed with 3×100 mL hot water, air
- customdried
- customrecrystallized from hot methanol
Sources & evidence
- ORD record
- ord-ee41a99fda2e4dfdba0470465bff74e9
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06054441
Reaction notes
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