ChemicalBook CAS DataBase List Tavaborole

Tavaborole synthesis

7synthesis methods

Product Name:Tavaborole
CAS Number:174671-46-6
Molecular formula:C7H6BFO2
Molecular Weight:151.93

Tavaborole, also known as AN-2690 (trade name Kerydin) is a topical antifungal medication for the treatment of onychomycosis, a fungal infection of the nail and nail bed. Tavaborole began its Phase 3 trials in December 2010 and was approved in July 2014. Tavaborole inhibits an essential fungal enzyme, Leucyl-tRNA synthetase, or LeuRS, required for protein synthesis. The inhibition of protein synthesis leads to termination of cell growth and cell death, eliminating the fungal infection. No treatment-related systemic side effects were observed in any of its clinical trials.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

Tavaborole synthesis

Baker, Stephen J.; Zhang, Yong-Kang; Akama, Tsutomu; Lau, Agnes; Zhou, Huchen; Hernandez, Vincent; Mao, Weimin; Alley, M. R. K.; Sanders, Virginia; Plattner, Jacob J. Discovery of a New Boron-?Containing Antifungal Agent, 5-?Fluoro-?1,?3-?dihydro-?1-?hydroxy-?2,?1-?benzoxaborole (AN2690)?, for the Potential Treatment of Onychomycosis. Journal of Medicinal Chemistry. Volume 49. Issue 15. Pages 4447-4450. Journal. (2006).

(4-Fluoro-2-(hydroxyMethyl)phenyl)boronic acid

1061223-45-7
58 suppliers
$28.00/100mg

174671-46-6
217 suppliers
$7.00/10mg

Yield:174671-46-6 81%

Reaction Conditions:

with sulfuric acid at 20; for 4 h;

Steps:

10
A mixture of crude (4-fluoro-2-(hydroxymethyl) phenyl)boronic acid (3 g) and 10% H2S04 solution (20 mL) is stirred at room temperature for 4 hrs. Water is added, and the mixture is extracted with ethyl acetate. The organic layer is washed with brine and dried on anhydrous sodium sulfate. The solvent is removed under reduced pressure, and the residue is treated with MTBE to afford benzo[c] [l,2]oxaborole-l,5(3H)-diol (Yield: 81%; Purity: 95%).

References:

BIOPHORE INDIA PHARMACEUTICALS PVT. LTD.;PULLAGURLA, Manik Reddy;NANDA KUMAR, Mecheril Valsan;PITTA, Bhaskar Reddy;RANGISETTY, Jagadeesh Babu WO2017/183043, 2017, A1 Location in patent:Page/Page column 34