Synthesis of 21‐diazoprogesterone‐6,7‐³H₂

Abstract

SUMMARYThe preparation of 21-diazoprogesterone-6, 7-3H2 is described. Progesterone was dehydrogenated with chloranil to give A-dehydroprogesterone. Degradation of the pregnane side-chain with sodium hypobromite gave the corresponding carboxylic acid. Catalytic reduction with carrier-free tritium followed by treatment with oxalyl chloride and then diazomethane afforded 21-diazoprogesterone-6, 7-3H2 with a specific activity of 42 Ci/mmol. (1) and 21-diazo-21-deoxycorticosterone-6,7-3H2 (7 Ci/mmol) (2).The utility of the 9a-bromo analog was limited, however, by its low specific activity. This report describes the procedure used to synthesize high-specific-activity 21-diazoprogesterone-6, 7-'H2.

Synthesis of 21-Diazo-9α-fluoro-16α-methyl-21-deoxy-[1,2(n)-3H]prednisolone

“…According to Chiu and Wolf ft 7 and (ii) the covalent binding of the photoaffmity label to the purified receptor*. Dodecyl sulfate polyacrylamide gel electrophoresis and fluorography showed only one tritiumlabelled band with a molecular weight of 90000l 2 ' 3 !.…”