124651-01-0

Basic information

• Product Name: 17-(N-t-butylcarboxamide)estra-1,3,5(10)-triene-3-carboxylic acid
• Synonyms: 17-(N-t-butylcarboxamide)estra-1,3,5(10)-triene-3-carboxylic acid
• CAS NO: 124651-01-0
• Molecular Formula: C24H33NO3
• Molecular Weight: 383.52372
• Mol File: 124651-01-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 582°Cat760mmHg
• Flash Point: 305.8°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 2.18E-14mmHg at 25°C
• Refractive Index: 1.559
• CAS DataBase Reference: 17-(N-t-butylcarboxamide)estra-1,3,5(10)-triene-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 17-(N-t-butylcarboxamide)estra-1,3,5(10)-triene-3-carboxylic acid(124651-01-0)
• EPA Substance Registry System: 17-(N-t-butylcarboxamide)estra-1,3,5(10)-triene-3-carboxylic acid(124651-01-0)

Safety Data

• Hazardous Substances Data: 124651-01-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C24H33NO3/c1-23(2,3)25-21(26)20-10-9-19-18-8-5-14-13-15(22(27)28)6-7-16(14)17(18)11-12-24(19,20)4/h6-7,13,17-20H,5,8-12H2,1-4H3,(H,25,26)(H,27,28)/t17-,18-,19+,20-,24+/m1/s1

Upstream product

• 124651-20-3 methyl 7β-estra-1,3,5(10)triene-3-carboxylate 
• 84510-05-4 17β-cyanoestra-1,3,5(10)-trien-3-ol 
• 156764-54-4 (8S,9S,13S,14S,17S)-3-Hydroxymethyl-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-17-carbaldehyde 
• 156764-53-3 Methyl 17β-cyano-estra-1,3,5(10)triene-3-carboxylate 
• 156764-52-2 Trifluoro-methanesulfonic acid (8S,9S,13S,14S,17S)-17-cyano-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl ester 
• 53-16-7 Estrone 
• 3381-23-5 (8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl methanesulfonate 
• 19915-20-9 17-cyano-3-hydroxyestra-1,3,5⁽¹⁰⁾-triene 3-methanesulfonate 
• 19915-19-6 17-cyano-3-hydroxyestra-1,3,5⁽¹⁰⁾,16-tetraene 3-methanesulfonate 
• 19915-17-4 17α-cyano-3,17β-dihydroxyestra-1,3,5(10)-triene 3-methanesulfonate 
• 151313-07-4 3-hydroxyestra-1,3,5(10)-triene-17β-carboxylic acid tert-butylamide 
• 151313-08-5 3-<(fluorosulfonyl)oxy>estra-1,3,5(10)-triene-17β-carboxylic acid tert-butylamide 
• 124651-19-0 methyl 17-(N-tert-butylcarbamoyl)estra-1,3,5⁽¹⁰⁾,16-tetraene-3-carboxylate 
• 124651-18-9 N-tert-butyl-3-<<(trifluoromethyl)sulfonyl>oxy>estra-1,3,5(10),16-tetraene-17-carboxamide 

Relevant articles and documents

A Novel, Practical Synthesis of Estra-1,3,5(10)-triene-3,17β-dicarboxylic Acid 17-tert-Butylamide (SK&F 105656) from Estrone, via a Palladium-Catalyzed Methoxycarbonylation of a 3-Fluorosulfonate

The title compound was prepared in nine steps from estrone in 22percent overall yield.Each step was performed on a 50-150 gal scale and 3.5 kg of the title compound was prepared.Estrone was converted to its 3-methanesulfonate with methanesulfonyl chloride.The 17-cyanohydrin was prepared using trimethylsilyl cyanide.Dehydration with phosphorus oxychloride/pyridine followed by Pd/C-catalyzed hydrogenation gave the 17β-cyano-3-hydroxyestra-1,3,5(10),16-tetraen-3-yl methanesulfonate derivative stereoselectively.Hydrolysis with sodium hydroxide in ethylene glycol gave a 3/1 β/α mixture of 17-carboxylic acid isomers.Reaction with Vilsmeier reagent and quenching into tert-butylamine, followed by selective crystallization, yielded the desired 3-hydroxyestra-1,3,5(10)-triene-17β-carboxylic acid tert-butylamide.Reaction with fluorosulfonic anhydride yielded the 3-fluorosulfonate.Palladium-catalyzed carbonylation in the presence of methanol gave the 3-carboxylic acid methyl ester, which was saponified to yield SK&F 105656.

Steroidal A ring aryl carboxylic acids: A new class of steroid 5α-reductase inhibitors

A series of 17β-carbamoyl-1,3,5(10)-estratriene-3-carboxylic acids has been prepared and evaluated in vitro as inhibitors of human and rat prostatic steroid 5α-reductase (EC 1.3.1.30). Potent inhibition of the human enzyme, in particular, was observed and preliminary studies using rat enzyme suggest that the inhibition results from the formation of an enzyme-NADP+-inhibitor complex. The compounds were synthesized from estrone, generally employing a differentiated bis-triflate carbonylation strategy.