US2020024621A1PendingUtilityA1
Enzymatic process for the preparation of (1s,2r)-2-(difluoromethyl)-1-(propoxycarbonyl)cyclopropanecarboxylic acid
Est. expiryJan 30, 2035(~8.5 yrs left)· nominal 20-yr term from priority
Inventors:Michael J. AbrahamsonAngelica B. KielbusWilliam T. RiordanDavid R. HillSanjay R. ChemburkarRajarathnam E. ReddyTimothy B. TowneJianzhang MeiStefan MixGareth Brown
C12P 41/005C12P 7/62C12Y 301/01003
57
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Claims
Abstract
Disclosed are methods of synthesizing enantioenriched difluoroalkylcyclopropyl amino esters and their salts, such as the dicyclohexylamine salt of (1S,2R)-2-(difluoromethyl)-1-(propoxycarbonyl)cyclopropane carboxylic acid. These compounds are useful intermediates in the synthesis of viral protease inhibitors.
Claims
exact text as granted — not AI-modified1 - 57 . (canceled)
58 . A method according to the following reaction scheme:
wherein R is alkyl; t-BuOH is tert-butyl alcohol; Boc is tert-butoxycarbonyl; and DPPA is diphenylphosphoryl azide.
59 . The method of claim 58 , wherein R is ethyl, propyl, or butyl.
60 . The method of claim 59 , wherein R is n-propyl.
61 . The method of claim 58 , wherein the starting material has the following structure:
62 . The method of claim 58 , wherein the hydrolysis step comprises treatment with aqueous LiOH.
63 . A compound having the following structure, or a pharmaceutically acceptable salt thereof:
64 . The compound of claim 63 , wherein the compound has the following structure:
65 . The compound of claim 64 , wherein R is ethyl, propyl, or butyl.
66 . The compound of claim 65 , wherein R is n-propyl.
67 . The compound of claim 64 , wherein the compound has the following structure:
68 . The compound of claim 64 , wherein the compound has the following structure:
69 . The compound of claim 68 , wherein R is ethyl, propyl, or butyl.
70 . The compound of claim 69 , wherein R is n-propyl.
71 . A compound having the following structure, or a pharmaceutically acceptable salt thereof:
wherein R is alkyl; and Boc is tert-butoxycarbonyl.
72 . The compound of claim 71 , wherein R is ethyl, propyl, or butyl.
73 . The compound of claim 72 , wherein R is n-propyl.
74 . The compound of claim 71 , wherein the compound has the following structure:
75 . The compound of claim 74 , wherein R is ethyl, propyl, or butyl.
76 . The compound of claim 75 , wherein R is n-propyl.
77 . A compound having the following structure, or a pharmaceutically acceptable salt thereof:
wherein Boc is tert-butoxycarbonyl.
78 . The compound of claim 77 , wherein the compound has the following structure:Join the waitlist — get patent alerts
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