Hydroxide → 3-Phenyl-3-(2,4,6-trichlorobenzenesulphonamido)propionic acid

HRID 850011Notes

Reaction equation

HRID 850011 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].[OH-].[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[C:16]=1[S:23](Cl)(=[O:25])=[O:24].[OH-].[Na+]>O1CCOCC1.[Na].O>[C:7]1([CH:2]([NH:1][S:23]([C:16]2[C:17]([Cl:22])=[CH:18][C:19]([Cl:21])=[CH:20][C:15]=2[Cl:14])(=[O:25])=[O:24])[CH2:3][C:4]([OH:6])=[O:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 961HydroxideHCID 14798Sodium HydroxideHCID 69189DL-beta-PhenylalanineHCID 5213352,4,6-Trichlorobenzenesulfonyl chloride

Product 1

HCID 230026243-Phenyl-3-(2,4,6-trichlorobenzenesulphonamido)propionic acidYield 73.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×HCID 5360545SodiumSolvent

Procedure

1.15 g of 3-amino-3-phenylpropionic acid are dissolved in 25 ml of dioxane and 7 ml of 1N sodium. hydroxide and 1.95 g of 2,4,6-trichlorobenzenesulphonyl chloride in 5 ml of dioxane are gradually added, while maintaining the pH at 10.5-11 by addition of 1N sodium hydroxide. After stirring for 2 hours at RT, the mixture is diluted with 100 ml of water, extracted twice with EtOAc and acidified to pH=2 by addition of 6N HCl. The solid formed is drained, washed with water and dried at 40° C. 2.09 g of the expected product are obtained, m.p.=218-219° C.

Workup

  1. temperaturewhile maintaining the pH at 10.5-11
  2. extractionextracted twice with EtOAc
  3. additionacidified to pH=2 by addition of 6N HCl
  4. customThe solid formed
  5. washwashed with water
  6. customdried at 40° C

Sources & evidence

ORD record
ord-71f6c85cb5e24c988e30b855d4a5de88
Source dataset
uspto-grants-2000_01
Patent number
US06015812

Reaction notes

Loading…