An efficient synthesis of deuterium-labeled degarelix acetate, a third-generation gonadotropin-releasing hormone receptor antagonist.

Degarelix acetate, a third-generation gonadotropin-releasing hormone receptor antagonist, shows great potential in the treatment of many androgen-related diseases. To support clinical studies of degarelix acetate, deuterium-labeled degarelix is highly desired for use as an internal standard. Using D2 O/D3 PO4 as a deuterium source, 2-amino-3-(naphthalen-2-yl)propanoic acid was converted to deuterated degarelix acetate in 13 steps and in 14% overall yield.