Synthesis of high specific activity tritium labelled 1S,2S-(-)-trans-2-isothiocyanato-N-methyl-N-[2-(1-pyrrolidinyl)-cyclohexyl]benzeneacetamide, a specific irreversible ligand for kappa opioid receptors
✍ Scribed by Brian R. De Costa; Andew Thurkauf; Richard R. Rothman; Arthur E. Jacobson; Kenner C. Rice
- Publisher
- John Wiley and Sons
- Year
- 1990
- Tongue
- French
- Weight
- 383 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
Abstract
Optically pure tritium labeled 1__S__,2__S__‐(‐)‐trans‐2‐isothiocyanato‐N‐methyl‐N‐[2‐(1‐pyrrolidinyl)cyclohexyl]benzeneacetamide, an affinity ligand specific for the kappa opioid receptor was synthesized from optically pure 1__S__,2__S__‐(‐)‐trans‐2‐amino‐N‐methyl‐N‐[2‐(1‐pyrrolidinyl)cyclohexyl]benzeneacetamide via the sequence of dibromination (57%) followed by catalytic tritiation of the dibromide. The resulting tritium labelled aniline (14% yield, specific activity 31.2 Ci/mmol) was transformed to the title compound in 13.3% yield and 99+% radiochemical purity by treatment with thiophosgene.