反応 #2186172

ord-eb1296fc119549d5812043015243cf3f

反応方程式

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

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

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

実験手順

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%).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07569225B2uspto-grants-2009_08