Water → HCID 18647977, compound

HRID 974686Notes

Reaction equation

HRID 974686 reaction equation
[CH2:1]([NH:18][C:19]([O:21][CH2:22][C@H:23]([OH:26])[CH2:24][OH:25])=[O:20])[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][CH3:17].[C:27]1([C:33](Cl)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[CH2:1]([NH:18][C:19]([O:21][CH2:22][C@H:23]([OH:26])[CH2:24][O:25][C:33]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:20])[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][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 18647978HCID 18647978, compound

Product 1

HCID 18647977HCID 18647977, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 12.03 g of 3 -O-(N-heptadecylcarbamoyl)-sn-glycerol (prepared as described in Preparation 15), 10.77 g of triphenylmethyl chloride and 10.8 ml of triethylamine dissolved in 240 ml of toluene was heated under reflux for 1.5 hours. After cooling, the reaction mixture was poured into water (0.5 liter) and then extracted twice with ethyl acetate. The combined extracts were washed with water, dried and concentrated by evaporation under reduced pressure. The resulting residue was dissolved in 240 ml of tetrahydrofuran. To the resulting solution was added 120 ml of a saturated aqueous solution of sodium bicarbonate, and the mixture was stirred at room temperature for 1 hour. After pouring the reaction mixture into water followed by extracting twice with ethyl acetate, the combined extracts were washed with water, dried and concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through 400 g of silica gel and to medium pressure liquid chromatography using an NQ-3 Packed Column (Wako pure Chemical Industry Co.). 15.89 g of the title compound were obtained from the fractions eluted with mixtures of hexane and diethyl ether ranging from 3:2 to 2:3 by volume as a viscous liquid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureAfter cooling
  4. extractionextracted twice with ethyl acetate
  5. washThe combined extracts were washed with water
  6. customdried
  7. concentrationconcentrated by evaporation under reduced pressure
  8. dissolutionThe resulting residue was dissolved in 240 ml of tetrahydrofuran
  9. additionTo the resulting solution was added 120 ml of a saturated aqueous solution of sodium bicarbonate
  10. additionAfter pouring the reaction mixture into water
  11. extractionby extracting twice with ethyl acetate
  12. washthe combined extracts were washed with water
  13. customdried
  14. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-ce57cfa65f4a47bc8d7d6946aae37619
Source dataset
uspto-grants-1991_11
Patent number
US05068340

Reaction notes

Loading…