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Synthesis of 1,1′-carbonyldimidazole-1-14C and its use in preparing a methoxy(polyethylene)glycol semicarbazide linker

✍ Scribed by Donald G. Walker; William H. Leister; Larry E. Weaner

Publisher
John Wiley and Sons
Year
1995
Tongue
French
Weight
377 KB
Volume
36
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Reaction of N‐(trimethylsilyl)imidazole (2) with phosgene‐^14^C in toluene afforded 92 w/w % pure (^1^H NMR) 1,1′‐carbonyldimidazole‐1‐^14^C (3) in near quantitative yield. Activation of MPEG‐amine 4 by reaction with 3 in dichloromethane afforded intermediate 5 in situ. Further reaction with hydrazine in toluene at 50°C and reprecipitation from 2‐propanol afforded crude 1 (81%). A two‐step chromatographic purification of this material followed by reprecipitation from 2‐propanol gave MPEG‐semicarbazide linker1. This material had a chemical purity estimated at 98%, a radiochemical purity of 95%, a specific activity of 7.7 μCi/mg (37.6 mCi/mmol) and a number‐average molecular weight of 4885 (^1^H NMR).

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