p-Toluenesulfonic acid → HCID 14206137, compound

HRID 329508Notes

Reaction equation

HRID 329508 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([NH:29][C:30](=[O:59])[O:31][C@@H:32]1[CH2:37][CH2:36][CH2:35][O:34][C@H:33]1[CH2:38][O:39]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C(=O)(O)[O-].[Na+]>CO>[CH2:12]([NH:29][C:30](=[O:59])[O:31][C@@H:32]1[CH2:37][CH2:36][CH2:35][O:34][C@H:33]1[CH2:38][OH:39])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 14482881HCID 14482881, compound

Product 1

HCID 14206137HCID 14206137, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

240.0 mg of p-toluenesulfonic acid were added to a solution of 2.753 g of (2S, 3R)-2-(triphenylmethoxymethyl)tetrahydropyran-3-yl N-heptadecylcarbamate (prepared as described in Preparation 27) dissolved in 55 ml of methanol, and the mixture was heated under reflux for 1 hour. At the end of this time, the reaction mixture was cooled, and 352.6 mg of sodium bicarbonate were added. The methanol was then removed by distillation under reduced pressure, and ethyl acetate was added. Insoluble materials were filtered off, and the filtrate was concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through 55 g of silica gel. 1.476 g of the title compound was obtained from those fractions eluted with mixtures of hexane and ethyl acetate ranging from 2:1 to 1:1 by volume in the form of crystals melting at 92.0°-93.5° C. (after recrystallisation from diethyl ether).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperatureAt the end of this time, the reaction mixture was cooled
  4. customThe methanol was then removed by distillation under reduced pressure, and ethyl acetate
  5. additionwas added
  6. filtrationInsoluble materials were filtered off
  7. concentrationthe filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-a66a3eb5653a4a75ab41c291f17f4d4a
Source dataset
uspto-grants-1990_01
Patent number
US04891363

Reaction notes

Loading…