4-Toluenesulfonyl chloride → HCID 86743644, compound

HRID 329529Notes

Reaction equation

HRID 329529 reaction equation
[CH2:1]([NH:18][C:19](=[O:39])[O:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][O:23][C@H:22]1[CH2:27][O:28][CH2:29][CH:30]([OH:38])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][OH:37])[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(N(CC)CC)C.[C:47]1([CH3:57])[CH:52]=[CH:51][C:50]([S:53](Cl)(=[O:55])=[O:54])=[CH:49][CH:48]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([NH:18][C:19](=[O:39])[O:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][O:23][C@H:22]1[CH2:27][O:28][CH2:29][CH:30]([OH:38])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][O:37][S:53]([C:50]1[CH:51]=[CH:52][C:47]([CH3:57])=[CH:48][CH:49]=1)(=[O:55])=[O:54])[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 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 70373784HCID 70373784, compound

Product 1

HCID 86743644HCID 86743644, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.458 g of dl-trans-2-[(2,8-dihydroxyoctyloxy)methyl]tetrahydropyran-3-yl N-heptadecylcarbamate (prepared as described in Preparation 75), 0.27 ml of triethylamine and 5 mg of 4-dimethylaminopyridine were dissolved in 10 ml of methylene chloride. 0.188 g of p-toluenesulfonyl chloride were added to the mixture, whilst ice-cooling, after which the mixture was stirred at room temperature for 14 hours. At the end of this time, the reaction mixture was washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through 12 g of silica gel and by medium pressure liquid chromatography through a Lobar B column. 0.492 g of the title compound was obtained, as a white wax, from the fractions eluted with mixtures of hexane and ethyl acetate ranging from 3:2 to 1:1 by volume.

Workup

  1. temperaturecooling
  2. washAt the end of this time, the reaction mixture was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe residue was purified by column chromatography through 12 g of silica gel and by medium pressure liquid chromatography through a Lobar B column

Sources & evidence

ORD record
ord-b39eb28adfba449590d30aca95138542
Source dataset
uspto-grants-1990_01
Patent number
US04891363

Reaction notes

Loading…