3-Oxo-4-aza-androst-1,5-diene-17-carboxylic Acid 21-b-Ethyl Carbonate

Ref. TR-O847185

Product Information

• Name: 3-Oxo-4-aza-androst-1,5-diene-17-carboxylic Acid 21-b-Ethyl Carbonate
• Synonyms: (Ethyl Carbonic) (4aR,4bS,6aS,7R,9aS,9bS)-4a,6a-Dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10-dodecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic Anhydride
• Brand: TRC

Description

Applications 3-Oxo-4-aza-androst-1,5-diene-17-carboxylic Acid 21-β-Ethyl Carbonate is an intermediate in the synthesis of 5,6-Dehydro-17α-dutasteride (D229570), which is an epimer of 5,6-Dehydro-17β-dutasteride (D229560) an impurity in the synthesis of Dutasteride (D735000), a dual inhibitor of 5α-reductase isoenzymes type 1 and 2; structurally related to Finasteride (F342000). Dutasteride is used in the treatment of benign prostatic hyperplasia.
References Bakshi, R.K., et al.: J. Med. Chem., 38, 3189 (1995); Gisleskog, P.O., et al.: Brit. J. Clin. Pharmacol., 47, 53 (1999); Djavan, B., et al.: Expert Opin. Pharmacother., 6, 311 (2005)

Chemical properties

• Molecular weight: 387.47
• Formula: C₂₂H₂₉NO₅
• Color/Form: Neat
• InChI: InChI=1S/C22H29NO5/c1-4-27-20(26)28-19(25)16-7-6-14-13-5-8-17-22(3,12-10-18(24)23-17)15(13)9-11-21(14,16)2/h8,10,12-16H,4-7,9,11H2,1-3H3,(H,23,24)/t13-,14-,15-,16-,21-,22+/m0/s1
• InChI key: InChIKey=SDKCLSVTZWQMTJ-FCAWPTKZSA-N
• SMILES: CCOC(=O)OC(=O)[C@@H]1CC[C@H]2[C@@H]3CC=C4NC(=O)C=C[C@]4(C)[C@H]3CC[C@@]21C