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- Title
Synthesis of stable‐isotope‐labeled N‐(3‐dimethylaminopropyl)‐N′‐ethylcarbodiimide and N‐(3‐dimethylaminopropyl)‐N′‐ethylurea.
- Authors
Cao, Kai; Brailsford, John A.; Bonacorsi, Samuel J.
- Abstract
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.
- Subjects
BRISTOL-Myers Squibb Co.; LIQUID chromatography-mass spectrometry; POTASSIUM cyanide; ETHYLENE glycol; CARBOXYLIC acids; AMINES
- Publication
Journal of Labelled Compounds & Radiopharmaceuticals, 2020, Vol 63, Issue 13, p526
- ISSN
0362-4803
- Publication type
Article
- DOI
10.1002/jlcr.3877