Water → 3-Octadecyl-2-morpholinocarbonyl-1-tritylglycerol

HRID 482947Notes

Reaction equation

HRID 482947 reaction equation
[CH2:1]([O:19][CH2:20][CH:21]([OH:43])[CH2:22][O:23][C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[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][CH3:18].[N:44]1[CH:49]=[CH:48]C=[CH:46][CH:45]=1.[C:50](Cl)(=O)[O:51]C1C=CC=CC=1.[OH2:60]>ClCCl>[CH2:1]([O:19][CH2:20][CH:21]([O:43][C:50]([N:44]1[CH2:45][CH2:46][O:60][CH2:48][CH2:49]1)=[O:51])[CH2:22][O:23][C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[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][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 15891Phenyl chloroformateHCID 128968481-(Octadecyloxy)-3-(triphenylmethoxy)propan-2-ol

Product 1

HCID 133124853-Octadecyl-2-morpholinocarbonyl-1-tritylglycerol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Octadecyl-1-tritylglycerol (2.93 g) and 0.8 g of pyridine were dissolved in 10 ml of dichloromethane, and, under ice-cooling and stirring, 0.78 g of phenyl chlorocarbonate was added dropwise. The mixture was stirred under ice-cooling for 30 minutes and at room temperature for an hour, followed by addition of 20 ml of dichloromethane and water. The organic layer was separated, washed with aqueous sodium hydrogen carbonate and water, and dried. The solvent was then distilled off and 5 ml of morpholine was added to the residue. The mixture was allowed to stand at room temperature overnight and the morpholine was distilled off. The residue was recrystallized from n-hexane to give 2.7 g of the above-identified compound melting at 78°-79° C.

Workup

  1. temperatureunder ice-cooling
  2. stirringThe mixture was stirred under ice-
  3. customThe organic layer was separated
  4. washwashed with aqueous sodium hydrogen carbonate and water
  5. customdried
  6. distillationThe solvent was then distilled off
  7. addition5 ml of morpholine was added to the residue
  8. distillationthe morpholine was distilled off
  9. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-1240add9bb414d96889ef77b8fea412b
Source dataset
uspto-grants-1986_03
Patent number
US04576933

Reaction notes

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