Réaction #58467

Équation de réaction

(RS)-4-{1-[5(4-Fluorophenyl)-2-methylthiazol4-yl]-methanoyl}-3-[2-(4-fluoro-phenyl)-2-oxo-ethoxycarbonylmethyl]-piperazine-1-carboxylic acid tert-butyl ester

tert-butyl carbamate

→

title compound

(RS)-4-{1-[5-(4-Fluorophenyl)-2-methylthiazol-4-yl]-methanoyl}-3-[4-(4-fluoro-phenyl)-oxazol-2-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester

Solvants

xylene

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling
2. 2
   Autrethe reaction mixture was partitioned between ethyl acetate and saturated sodium hydrogen carbonate solution
3. 3
   SéchageThe organic layer was dried (MgSO4)
4. 4
   Autreevaporated
5. 5
   Autrethe residue chromatographed over silica gel
6. 6
   LavageElution with a gradient of 25 to 100% ethyl acetate in hexane

Mode opératoire

(RS)-4-{1-[5(4-Fluorophenyl)-2-methylthiazol4-yl]-methanoyl}-3-[2-(4-fluoro-phenyl)-2-oxo-ethoxycarbonylmethyl]-piperazine-1-carboxylic acid tert-butyl ester, description 111 (0.385 g), tert-butyl carbamate (0.376 g) and boron trifluoride etherate (4 drops) were dissolved in xylene (5 ml) and heated to 140° C., under argon and with stirring for 48 hours. After cooling, the reaction mixture was partitioned between ethyl acetate and saturated sodium hydrogen carbonate solution. The organic layer was dried (MgSO4), evaporated and the residue chromatographed over silica gel. Elution with a gradient of 25 to 100% ethyl acetate in hexane provided the title compound as a pale yellow oil (0.130 g), mass spectrum (API+) 581 [MH+], C30H30F2N4O4S requires 580.

Source