Route development and multikilogram GMP delivery of a somatostatin receptor antagonist
Route development and demonstration on multikilogram scale for the first GMP delivery of MK-4256 are described. Key aspects of the convergent route include a regioselective green iodination, one-pot oxadiazole synthesis, and an efficient ketone Pictet-Spengler reaction with diastereomeric upgrade via crystallization to afford 6 kg of API. A recycle procedure augmented the yield of desired diastereomer in the Pictet-Spengler reaction from a mixture of diastereomers heavily enriched in the undesired diastereomer.
Ruck, Rebecca T.,Huffman, Mark A.,Stewart, Gavin W.,Cleator, Ed,Kandur, Wynne V.,Kim, Mary M.,Zhao, Dalian
p. 1329 - 1337
(2012/10/29)
Nitrosation of methyl 2-acylamino-3-dimethylaminopropenoates. A simple conversion of N-acylglycines into 5-substituted 1,2,4-oxadiazole-3-carboxylates
A novel simple synthesis of 5-substituted-1,2,4-oxadiazole-3-carboxylates 5 from N-acylglycines 1, which are transformed with DMF in the presence of phosphorus oxychloride into 2-substituted-4-dimethylaminomethyleneoxazol-5(4H)-ones 2, followed by opening
Kmetic,Stanovnik
p. 1563 - 1565
(2007/10/03)
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