Pyridine → 3-(N-docosylcarbamoyloxy)-2-methoxy-1-propanol

HRID 1380566Notes

Reaction equation

HRID 1380566 reaction equation
C(O)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.[N:43]1[CH:48]=CC=CC=1.[CH3:49][O:50][CH:51]([CH2:54][OH:55])[CH2:52][OH:53]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH2:2]([NH:43][C:48]([O:53][CH2:52][CH:51]([O:50][CH3:49])[CH2:54][OH:55])=[O:33])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 1049PyridineHCID 17085Tricosanoic AcidHCID 199401P,P-Diphenylphosphinic azideHCID 111709312-Methoxypropane-1,3-diol

Product 1

HCID 233252793-(N-docosylcarbamoyloxy)-2-methoxy-1-propanolYield 47%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

In a mixture of 70 ml of dry toluene and 3.6 ml of triethylamine is dissolved 7.08 g (2×10-2 moles) of tricosanoic acid, and 6.6 g (2.4×10-1 moles) of diphenylphosphorylazide is added dropwise at room temperature. The mixture is stirred at room temperature for 3 hours, concentrated to one-third of its original volume, and refluxed for 1.5 hours. After cooling, 30 ml of pyridine and 7.84 g (7.4×10-2 moles) of 2-methoxy-1,3-propyleneglycol. The mixture is stirred at room temperature overnight and concentrated to dryness under reduced pressure. Water is added to the residue, followed by extraction with chloroform. The chloroform layer is washed with water and dried over sodium sulfate. The solvent is then distilled off and the residue is purified by silica gel (100 g) column chromatography. The chloroform eluate fraction is concentrated to dryness to give 4.3 g (47%) of 3-(N-docosylcarbamoyloxy)-2-methoxy-1-propanol as a colorless powder.

Workup

  1. additionis added dropwise at room temperature
  2. concentrationconcentrated to one-third of its original volume
  3. temperaturerefluxed for 1.5 hours
  4. temperatureAfter cooling
  5. stirringThe mixture is stirred at room temperature overnight
  6. concentrationconcentrated to dryness under reduced pressure
  7. additionWater is added to the residue
  8. extractionfollowed by extraction with chloroform
  9. washThe chloroform layer is washed with water
  10. dry with materialdried over sodium sulfate
  11. distillationThe solvent is then distilled off
  12. customthe residue is purified by silica gel (100 g) column chromatography
  13. concentrationThe chloroform eluate fraction is concentrated to dryness

Sources & evidence

ORD record
ord-850759655ddb4523963b90f7c2a49fad
Source dataset
uspto-grants-1986_04
Patent number
US04582824

Reaction notes

Loading…