Pyridine → HCID 22808837, compound

HRID 905352Notes

Reaction equation

HRID 905352 reaction equation
[Si:1]([CH:8]([OH:24])[C@H:9]1[O:13][C@@H:12]([N:14]2[CH2:19][N:18]([CH3:20])[C:17](=[O:21])[NH:16][C:15]2=[O:22])[CH2:11][C@@H:10]1[OH:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:31](Cl)(=[O:43])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.O>[Si:1]([CH:8]([OH:24])[C@H:9]1[O:13][C@@H:12]([N:14]2[CH2:19][N:18]([CH3:20])[C:17](=[O:21])[NH:16][C:15]2=[O:22])[CH2:11][C@:10]1([C:31](=[O:43])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[OH:23])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8166Dodecanoyl chlorideHCID 516892Sodium BicarbonateHCID 22808836HCID 22808836, compound

Product 1

HCID 22808837HCID 22808837, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
10 °C

Procedure

To a solution consisting of 3.59 gm. (0.010 mole) of 1-(5-tert-butyldimethylsilyl-2-deoxy-β-D-ribofuranosyl)-5-methyl-5,6-dihydro-s-triazine-2,4-(1H,3H)-dione and 30 ml. A.R. pyridine that had been cooled to 5° C. was added, with stirring, 2.55 gm. (0.0116 mole) of freshly distilled lauroyl chloride. This reaction mixture was stirred for 18 hours at 25° C. Then it was cooled to 10° C. and 3 ml. water was added. This mixture was stirred at 25° C. while the solvents were removed by evaporation under reduced pressure. The residue thus obtained was dispersed in a solvent mixture consisting of 100 ml. chloroform and 50 ml. saturated aqueous sodium bicarbonate. The aqueous and organic phases were allowed to stabilize and the organic phase was saved. It was washed two times with 50 ml. portions of saturated aqueous sodium bicarbonate and dried over anhydrous magnesium sulfate. The dried chloroform solution was filtered and the filter was washed with chloroform. The filtrate and washings were combined and the chloroform was removed by evaporation under reduced pressure. There was thus obtained 4.8 gm. (88.7% yield) of 1-(5-tert-butyldimethylsilyl-3-lauroyl-2-deoxy-β-D-ribofuranosyl)-5,6-dihydro-5-methyl-s-triazine-2,4-(1H,3H)-dione.

Workup

  1. additionwas added
  2. stirringThis reaction mixture was stirred for 18 hours at 25° C
  3. stirringThis mixture was stirred at 25° C. while the solvents
  4. customwere removed by evaporation under reduced pressure
  5. customThe residue thus obtained
  6. additionwas dispersed in a solvent mixture
  7. washIt was washed two times with 50 ml
  8. dry with materialportions of saturated aqueous sodium bicarbonate and dried over anhydrous magnesium sulfate
  9. filtrationThe dried chloroform solution was filtered
  10. washthe filter was washed with chloroform
  11. customthe chloroform was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-61d3ea48cc03488eb55b7efa5d43e52b
Source dataset
uspto-grants-1983_12
Patent number
US04423212

Reaction notes

Loading…