Synthesis of Monobactam Cannabinoid Conjugates

Example 20

Monobactam thiocarbonate linked β-lactam antibiotic cannabinoid conjugate components are synthesized according to the following Scheme. The starting material [76855-69-1] is deacetylated under reported conditions (Journal of Fluorine Chemistry, 72(2), 255-9; 1995) to give the 2-hydroxy intermediate. This hydroxy group is then reacted with thiophosgene and a cannabinoid (CBD) under standard basic conditions to form the carbonate link. Removal of the silyl ether protecting group followed by sulfonation using established conditions gives the product.

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US11877988B2. Conjugate molecules (2024-01-23). Diverse Biotech, Inc. [US]. Inventors: Paul Hershberger [US], Philip Arlen [US].

Patent 2024

Cannabinoid Carbonate Ether Fluorine Thiophosgene β lactam antibiotic

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Variable analysis

independent variables

Deacetylation of the starting material [76855-69-1] under reported conditions
Reaction of the 2-hydroxy intermediate with thiophosgene and a cannabinoid (CBD) under standard basic conditions
Removal of the silyl ether protecting group
Sulfonation using established conditions

dependent variables

Synthesis of the monobactam thiocarbonate linked β-lactam antibiotic cannabinoid conjugate components

control variables

The reported conditions for deacetylation
The standard basic conditions for the reaction with thiophosgene and CBD
The established conditions for sulfonation

controls

No positive or negative controls were explicitly mentioned in the provided information.

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