Details

Autor(en) / Beteiligte

• Cao, Kai
• Brailsford, John A.
• Bonacorsi, Samuel J.

Titel

Synthesis of stable‐isotope‐labeled N‐(3‐dimethylaminopropyl)‐N′‐ethylcarbodiimide and N‐(3‐dimethylaminopropyl)‐N′‐ethylurea

Ist Teil von

• Journal of labelled compounds & radiopharmaceuticals, 2020-11, Vol.63 (13), p.526-530

Ort / Verlag

England: Wiley Subscription Services, Inc

Erscheinungsjahr

2020

Quelle

Wiley Online Library

Beschreibungen/Notizen

• Summary N‐(3‐Dimethylaminopropyl)‐N′‐ethylcarbodiimide (EDC) is a carbodiimide coupling reagent commonly used for the preparation of amides from carboxylic acids and amines. Because of initial concerns regarding the genotoxicity of EDC and its use in GMP syntheses at Bristol Myers Squibb, the quantitation of residual EDC and its by‐product N‐(3‐dimethylaminopropyl)‐N′‐ethylurea (EDU) by liquid chromatography–mass spectrometry (LCMS) impurity analysis was required. These analyses required the use of stable‐isotope‐labeled EDC and EDU to serve as internal standards. To meet this need, stable‐isotope‐labeled EDC 9 and EDU 10 were prepared from [1,2‐13C2] ethylene glycol and [13C,15N] potassium cyanide in overall yields of 6% and 8%, respectively. Due to concerns regarding the genotoxicity of EDC, and its common use in API synthesis, the quantitation of residual EDC and its by‐product EDU by LCMS impurity analysis was needed, which required the use of stable‐isotope labeled EDC and EDU as internal standards. To meet this need, stable isotope labelled EDC 9 and EDU 10 were prepared from [1,2‐13C2] ethylene glycol and [13C,15N] potassium cyanide in overall yields of 6% and 8% respectively.