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Method for carbamoylating alcohols

A kind of technology of alcohol carbamoyl and methanesulfonic acid, applied in the field of carbamoylation

Inactive Publication Date: 2004-04-14
WARNER-LAMBERT CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, there are only two sources of commercialized CSI, neither of which is domestically produced in the United States

Method used

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  • Method for carbamoylating alcohols
  • Method for carbamoylating alcohols
  • Method for carbamoylating alcohols

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Love and Kormendy's method

[0040] Loev and Kormendy (supra, 1963) used trifluoroacetic acid and sodium cyanate for carbamylation of alcohols. Studies of the carbamoylation of alcohols containing a thiocarbyl group and a basic moiety were initiated with these reagents.

[0041] Materials and methods

[0042] Capravirine thiols

[0043] In this study, the alcohol was the thiol precursor of the antiviral agent Capravirine. Capravirine hydrocarbon thiols are prepared by:

[0044] Benzyloxy((4-isopropyl-1-(4-pyridyl)methyl)-1H-imidazol-2-yl)-hydrogen oxalate (171.6 g, 0.342 moles) in toluene (460 mL) and water (150 mL) to make a slurry. The mixture was stirred and cooled to below 10°C. The mixture was slowly cooled to a final pH of 11-12 by adding 32% aqueous potassium hydroxide (KOH). The organic layer was separated and washed with water and then saturated sodium chloride solution. Benzyloxy((4-isopropyl-1-(4-pyridyl)methyl)-1H-imidazol-2-yl)-methane in toluene...

Embodiment 2

[0052] Carbamylation of alcohols with sodium cyanate in the presence of sulfuric acid or acetic acid

[0053] The carbamoylation of alcohols containing thiol and base moieties with sodium cyanate was studied in the presence of sulfuric or acetic acid.

[0054] Materials and methods

[0055] Capravirine mercaptans were obtained as described in Example 1 above. Also as described in Example 1, the other reactants were all the finest commercial grades and were used without further purification.

[0056] The conversion of Capravirine thiols to Capravirine was carried out as described in Example 1 with the difference that sulfuric acid or acetic acid was used instead of TFA. Therefore, the slurry was cooled to -10°C, then sulfuric acid (18 mL), or acetic acid (30 mL) was added dropwise while keeping the temperature below 0°C.

[0057] result

[0058] Sulfuric acid and acetic acid provided higher yields than TFA. The conversion of carbamylated alcohols in this process was 1...

Embodiment 3

[0060] Carbamylation of alcohols with sodium cyanate in the presence of methanesulfonic acid

[0061] The carbamoylation of alcohols with sodium cyanate was studied under various reaction conditions in the presence of acid to arrive at a suitable method.

[0062] Materials and methods

[0063] Material

[0064] Capravirine mercaptans were obtained as described in Example 1 above. Also as described in Example 1, the other reactants were all the finest commercial grades and were used without further purification.

[0065] Preparation of Capravirine

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Abstract

The present invention includes a method for carbamoylating an alcohol with sodium cyanate in the presence of methanesulfonic acid. The reaction can be conducted under anhydrous conditions. This method is suitable for carbamoylating a molecule including both an alcohol moiety and a basic moiety or a molecule including both an alcohol moiety and a sulfenyl moiety, such as the sulfenyl alcohol precursor of the antiviral agent Capravirine.

Description

field of invention [0001] The present invention includes the carbamoylation of alcohols with sodium cyanate in the presence of methanesulfonic acid. The reaction can be performed under anhydrous conditions. This method is suitable for the carbamoylation of a molecule comprising both an alcohol moiety and a base moiety and / or a molecule comprising both an alcohol moiety and a sulfenyl moiety, such as the antiviral agent Capravirine Hydrocarbyl thiol precursor. Background of the invention [0002] A non-nucleoside reverse transcriptase inhibitor called Capravirine can be synthesized by using chlorosulfonyl isocyanate (CSI) to convert the penuitimate Capravirine hydrocarbon thiol into the corresponding carbamate, Capravirine. CSI gives high yields of carbamoylated alcohols under the desired conditions, but has special shipping and handling requirements due to its high reactivity with water. In addition, there are only two sources of commercialized CSI, neither of which is do...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B61/00C07C269/00C07C269/02C07D401/06
CPCC07D401/06C07C269/00
Inventor 詹姆斯·E·埃利斯
Owner WARNER-LAMBERT CO
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