p-Toluenesulfonic acid → HCID 54413865, compound

HRID 1279155Notes

Reaction equation

HRID 1279155 reaction equation
[C:1]([NH:14][C@H:15]([C:17]([OH:19])=[O:18])[CH3:16])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:20]([CH:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:29]O)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>>[CH2:20]([CH:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:29][O:18][C:17](=[O:19])[C@H:15]([CH3:16])[NH:14][C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 214142-OctyldodecanolHCID 516892Sodium BicarbonateHCID 13854541N-LAUROYL-L-ALANINE

Product 1

HCID 54413865HCID 54413865, compoundYield 91.1%

Conditions

Temperature
130 °C

Procedure

N-Lauroylalanine (10 g) and 9.5 g of 2-octyldodecanol were charged in a 200-ml flask, and thereto was added 0.5 g of p-toluenesulfonic acid as the catalyst. The mixture was maintained at 130° C. for 3 hours for reaction. To the reaction mixture was added about 200 ml of a aqueous saturated solution of sodium hydrogen carbonate, and the resulting aqueous layer was removed. The oily layer was further washed with water. The extracted oily layer was well dried by adding 5 g of anhydrous magnesium sulfate thereto, and the magnesium sulfate was then filtered off to give 16 g (yield: 82%) of a liquid product.

Workup

  1. customthe resulting aqueous layer was removed
  2. washThe oily layer was further washed with water
  3. customThe extracted oily layer was well dried
  4. additionby adding 5 g of anhydrous magnesium sulfate
  5. filtrationthe magnesium sulfate was then filtered off

Sources & evidence

ORD record
ord-e43532730b92496aa06154c46a74c614
Source dataset
uspto-grants-2002_09
Patent number
US06447790B1

Reaction notes

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