Reaction #470379

Reaction equation

Triethylamine

L-cysteine hydrochloride

3-bromo-propan-1,2-diol

methanol

→

S-(2,3-dihydroxypropyl)cysteine

Solvents

water

acetone

water

Conditions

Workup

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

Procedure

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