Pyridine → 2-(N,N-Dimethylcarbamoyl)-3-octadecyl-1-tritylglycerol

HRID 482944Notes

Reaction equation

HRID 482944 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]=CC=C[CH:45]=1.[C:50](Cl)(=O)[O:51]C1C=CC=CC=1.C(Cl)(Cl)Cl>ClCCl.O>[CH3:45][N:44]([CH3:49])[C:50]([O:43][CH:21]([CH2:20][O:19][CH2:1][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])[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)=[O:51]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6212ChloroformHCID 15891Phenyl chloroformateHCID 128968481-(Octadecyloxy)-3-(triphenylmethoxy)propan-2-ol

Product 1

HCID 133124842-(N,N-Dimethylcarbamoyl)-3-octadecyl-1-tritylglycerolYield 100.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-Octadecyl-1-tritylglycerol (2.6 g, 4.43 mmol) and 0.7 g (8.86 mmol) of pyridine were dissolved in 9 ml of dichloromethane, and 0.69 g of phenyl chlorocarbonate was added dropwise. The solution was stirred at room temperature for 30 minutes, and then stirred with 25 ml of chloroform and 25 ml of water. The aqueous layer was discarded and the organic layer was washed with 1% sodium hydrogen carbonate solution, dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was dissolved in 13 ml of dichloromethane, and dimethylamine gas was bubbled into the solution. The solution was concentrated to dryness under reduced pressure and the residue was purified by column chromatography on silica gel (20 g) using n-hexane-ethyl acetate (9:1) as the eluent to give 2.92 g (100%) of colorless needles, melting at 57.5°-58.0° C.

Workup

  1. washthe organic layer was washed with 1% sodium hydrogen carbonate solution
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness under reduced pressure
  4. dissolutionThe residue was dissolved in 13 ml of dichloromethane
  5. customdimethylamine gas was bubbled into the solution
  6. concentrationThe solution was concentrated to dryness under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (20 g)

Sources & evidence

ORD record
ord-3284137b6e224420b7c21bbcc1a7c010
Source dataset
uspto-grants-1986_03
Patent number
US04576933

Reaction notes

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