Pyridine → HCID 86742233, compound

HRID 580057Notes

Reaction equation

HRID 580057 reaction equation
[OH:1][CH:2]([CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:3][O:4][P:5](=[O:8])([OH:7])[OH:6].S(Cl)(Cl)=O.N1C=CC=CC=1.C([N:40](C(CC1C=CC=CC=1)=O)[C@H:41]([C:44]([OH:46])=[O:45])[CH2:42]O)C1C=CC=CC=1>C(Cl)(Cl)Cl.[Pd].O>[NH2:40][CH:41]([C:44]([OH:46])=[O:45])[CH2:42][O:8][P:5](=[O:6])([OH:7])[O:4][CH2:3][CH:2]([OH:1])[CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

8

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 17855154HCID 17855154, compoundHCID 70415240HCID 70415240, compound

Product 1

HCID 86742233HCID 86742233, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Dichlorophosphoridate was obtained by using 100.0 g (0.29 mol) of mono(2-hydroxy-3-lauryloxypropyl) phosphoric acid and 105.0 g (0.88 mol) of thionyl chloride. Then, 55.4 g (0.70 mol) of pyridine and 179.6 g (0.52 mol) of benzyl-N-benzylcarbonyl serine were dissolved in 100 ml of chloroform and stirred at 0° C. for 4 hours. Then, the reaction temperature was raised to room temperature and agitation was effected for 4 hours. After the reaction was completed, 100 ml of water were added and stirred at 20° C. for one hour. Then, the solvent was distilled off and the residue was extracted from ethylether. The thus obtained residue was dissolved in methanol and hydrogen was blown while refluxing methanol by heating to effect hydrogenation reaction for about 10 hours at a normal pressure by using a palladium/carbon catalyst at a normal pressure. After the reaction was completed, the residue obtained by distilling off methanol was purified on silica gel column chromatography (eluent/chloroform:methanol=90:10), to obtain 39.7 g of aimed 2-amino-2-carboxyethyl-(2-hydroxy-3-lauryloxypropyl) phosphoric acid as a white solid (0.09 mol, yield 32.0%).

Workup

  1. customDichlorophosphoridate was obtained
  2. temperatureThen, the reaction temperature was raised to room temperature
  3. waitagitation was effected for 4 hours
  4. stirringstirred at 20° C. for one hour
  5. distillationThen, the solvent was distilled off
  6. extractionthe residue was extracted from ethylether
  7. dissolutionThe thus obtained residue was dissolved in methanol
  8. temperaturewhile refluxing methanol
  9. temperatureby heating
  10. customreaction for about 10 hours at a normal pressure
  11. customthe residue obtained
  12. distillationby distilling off methanol
  13. customwas purified on silica gel column chromatography (eluent/chloroform:methanol=90:10)

Sources & evidence

ORD record
ord-2ae40aeb1cf84b1591ccc71e63b97857
Source dataset
uspto-grants-1988_06
Patent number
US04751320

Reaction notes

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