Reacción #58464

Ecuación de reacción

9-Fluorenylmethoxycarbonyl chloride

hydrochloric acid

3-Methoxycarbonylmethylpiperazine-1-carboxylic acid tert-butyl ester

hydrochloric acid

→

title compound

(RS)-2-Carboxymethylpiperazine-1,4-dicarboxylic acid 4-tert-butyl ester 1-(9H-fluoren-9-ylmethyl) ester

Disolventes

sodium hydroxide

NaOH

—

TBF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturamaintaining the pH at 9-10
2. 2
   ExtracciónThe solution was extracted with ethyl acetate (×2)
3. 3
   Secadodried (MgSO4)
4. 4
   Otroevaporated

Procedimiento

3-Methoxycarbonylmethylpiperazine-1-carboxylic acid tert-butyl ester (6.0 g) was dissolved in TBF (60 ml) and 1N sodium hydroxide solution (60 ml) and stirred at room temperature for 6 hours. The solution was then cooled to 5° C. and adjusted to pH 9-10 by the addition of 10% hydrochloric acid. Nα(9-Fluorenylmethoxycarbonyl chloride (6.05 g) was then added portionwise, maintaining the pH at 9-10 by the addition of 1N NaOH solution. The reaction mixture was stirred at 5° C. for 16 hours. The solution was then adjusted to pH 1 by the addition of 10% hydrochloric acid. The solution was extracted with ethyl acetate (×2), dried (MgSO4) and evaporated. The title compound was obtained as a white foam (9.96 g), mass spectrum (API+) 411 [(M-C4H8)H+], C26H30N2O6 requires 466.

Fuente