Réaction #470379

Équation de réaction

Triethylamine

L-cysteine hydrochloride

3-bromo-propan-1,2-diol

methanol

→

S-(2,3-dihydroxypropyl)cysteine

Solvants

water

acetone

water

Conditions de réaction

Traitement

1. 1
   Autrewas reduced in vacuo at 40° C. to a white residue which
2. 2
   Autrethe precipitate isolated by centrifugation
3. 3
   AutreThe precipitate was purified by several precipitations from water with acetone

Mode opératoire

Triethylamine (6 g, 8.2 ml, 58 mmoles) was added to L-cysteine hydrochloride (3 g, 19 mmole) and 3-bromo-propan-1,2-diol (4.2 g, 2.36 ml, 27 mmole) in water and the homogeneous solution kept at room temperature for 3 days. The solution was reduced in vacuo at 40° C. to a white residue which was boiled with methanol (100 ml), centrifuged and the residue dissolved in water (5 ml). This aqueous solution was added to acetone (300 ml) and the precipitate isolated by centrifugation. The precipitate was purified by several precipitations from water with acetone to give S-(2,3-dihydroxypropyl)cysteine as a white amorphous powder (2.4 g, 12.3 mmol, 64.7%).

Source