Synthesis of [ 14 C]ABT‐418, a cholinergic channel activator labeled at two sites on the isoxazole ring | Zendy

Surber Bruce W. | Zendy; Elliott Richard L. | Zendy; Kopecka Hana | Zendy; Thomas Samuel B. | Zendy

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Synthesis of [ 14 C]ABT‐418, a cholinergic channel activator labeled at two sites on the isoxazole ring

Author(s) -

Surber Bruce W.,

Elliott Richard L.,

Kopecka Hana,

Thomas Samuel B.

Publication year - 1996

Publication title -

journal of labelled compounds and radiopharmaceuticals

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.432

H-Index - 47

eISSN - 1099-1344

pISSN - 0362-4803

DOI - 10.1002/(sici)1099-1344(199609)38:9<857::aid-jlcr897>3.0.co;2-u

Subject(s) - chemistry , isoxazole , hydrochloride , acetone , ring (chemistry) , oxime , medicinal chemistry , sodium acetate , cholinergic , stereochemistry , organic chemistry , neuroscience , biology

[ 14 C]ABT‐418, (S)‐3‐[ 14 C]methyl‐5‐[N‐methyl‐2‐pyrrolidinyl][4‐ 14 C]isoxazole hydrochloride, was labeled in two positions at maximum specific activity. Starting with 100 mCi of sodium [2‐ 14 C]acetate, 14.6 mCi at 105 mCi/mmol was obtained in 8 steps including the formation of [1,3‐ 14 C]acetone in the pyrolysis of barium [2‐ 14 C]acetate. The key step was the formation of the dianion of [1,3‐ 14 C]acetone oxime and its condensation with L‐proline methyl ester.

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