تفاعل #470379

ord-4b4c109375b5444f8c2a60926d4e81e9

معادلة التفاعل

CCN(CC)CC
Triethylamine
Cl.N[C@@H](CS)C(=O)O
L-cysteine hydrochloride
OCC(O)CBr
3-bromo-propan-1,2-diol
CO
methanol
N[C@@H](CSCC(O)CO)C(=O)O
S-(2,3-dihydroxypropyl)cysteine

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08367067B2uspto-grants-2013_02