Palmitoyl chloride → HCID 178443055, compound

HRID 1005358Notes

Reaction equation

HRID 1005358 reaction equation
[C@@H:1]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([OH:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[C:20](Cl)(=[O:36])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>CN(C1C=CN=CC=1)C.CN(C)C=O>[C:20]([C@@:1]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([OH:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3])(=[O:36])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 2

HCID 8206Palmitoyl chlorideHCID 178521066(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-hydroxypurin-9-yl)oxolane-3,4-diol

Product 1

HCID 178443055HCID 178443055, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a 50 mL flask was added inosine (1.0 g, 3.73 mmol) and N,N-dimethyl-4-aminopyridine (0.017 g, 0.074 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 (1.3 mL, 4.1 mmol) was added dropwise. The mixture was allowed to stir while it slowly warmed to 25° C. After 18 h, the mixture was quenched with a small chunk of ice and the solvents were evaporated leaving a white gum. Toluene (20 mL) was evaporated from the gum, which was then thoroughly triturated with 1:1 ethyl acetate-diethyl ether. The supernatant was isolated by suction filtration and the solvents evaporated leaving a syrup which turned into a soft, amorphous solid after 24 h in a vacuum desiccator.

Workup

  1. customthe flask was purged with argon gas and pyridine (8 mL)
  2. additionwas added via cannula
  3. temperatureto cool 10 min. in an ice/NaCl bath
  4. stirringto stir while it
  5. customthe mixture was quenched with a small chunk of ice
  6. customthe solvents were evaporated
  7. customleaving a white gum
  8. customToluene (20 mL) was evaporated from the gum, which
  9. customwas then thoroughly triturated with 1:1 ethyl acetate-diethyl ether
  10. customThe supernatant was isolated by suction filtration
  11. customthe solvents evaporated
  12. customleaving a syrup which
  13. customafter 24 h

Sources & evidence

ORD record
ord-9d7ed5678fc6414593c75f8180d94017
Source dataset
uspto-grants-2000_04
Patent number
US06054441

Reaction notes

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