Réaction #312134

ord-e24802aca7804039894ced150709acc9

Équation de réaction

CCCCC(Br)C(=O)OC
2-bromohexanoic acid methyl ester
N#C[O-].[K+]
potassium cyanate
CO
methanol
CCCCC(NC(=O)OC)C(=O)OC
2-methoxycarbonylaminohexanoic acid methyl ester
Rendement 75.6%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    FiltrationAfter the cooling off of the reaction mixture the salts were filtered off
  2. 2
    Concentrationthe filtrate concentrated in a vacuum
  3. 3
    Filtrationthe undissolved material filtered off
  4. 4
    workup.DISTILLATIONSubsequently the acetone was distilled off

Mode opératoire

14.63 grams of 2-bromohexanoic acid methyl ester, 8.52 grams of potassium cyanate and 7.85 grams of methanol were heated in 70 ml of dimethylformamide (DMF) at 100° C. for 45 minutes under vigorous stirring. After the cooling off of the reaction mixture the salts were filtered off and the filtrate concentrated in a vacuum. The viscous residue was taken up with 50 ml of acetone and the undissolved material filtered off. Subsequently the acetone was distilled off and the residue fractionated in the high vacuum. There resulted 10.75 grams (75.5%) of 2-methoxycarbonylaminohexanoic acid methyl ester having a boiling point of 78° C./0.007 mbar.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04234744uspto-grants-1980_11