(-)-1-(2,3,4-Trichlorophenyl)ethanesulfonic acid → HCID 131719026, compound

HRID 21734Notes

Reaction equation

HRID 21734 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[CH:10]([S:12]([OH:15])(=[O:14])=[O:13])[CH3:11].Cl.[NH2:17][CH2:18][CH:19]([SH:24])[CH2:20][C:21]([OH:23])=[O:22]>O>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[CH:10]([S:12]([OH:15])(=[O:14])=[O:13])[CH3:11].[NH2:17][CH2:18][C@H:19]([SH:24])[CH2:20][C:21]([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 11055367(-)-1-(2,3,4-Trichlorophenyl)ethanesulfonic acidHCID 88300245Racemic 4-amino-3-mercaptobutyric acid hydrochloride

Product 1

HCID 131719026HCID 131719026, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

(-)-1-(2,3,4-Trichlorophenyl)ethanesulfonic acid (3.18 g) is dissolved in water (17.4 ml), and thereto is added aqueous solution of racemic 4-amino-3-mercaptobutyric acid hydrochloride (3.77 g)in water (24.6 ml). The mixture is dissolved at 70° C.-80° C., and allowed to cool. After cooling, the mixture is stirred under ice-cooling for one hour, and the precipitated crystals are collected by filtration, washed, and dried to give (3R)-4-amino--3-mercaptobutyric acid (-)-1-(2,3,4-trichlorophenyl)ethanesulfonate (3.8 g).

Workup

  1. dissolutionThe mixture is dissolved at 70° C.-80° C.
  2. temperatureto cool
  3. temperatureAfter cooling
  4. temperaturecooling for one hour
  5. filtrationthe precipitated crystals are collected by filtration
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-3b02d0f0c2cc4269acc3e0de4a1d9141
Source dataset
uspto-grants-1995_06
Patent number
US05424446

Reaction notes

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