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Preparation of methyl 3-(benzyloxy)-5-((2,4-difluorobenzyl)carbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate Disclosure Number: IPCOM000239636D
Publication Date: 2014-Nov-20
Document File: 1 page(s) / 139K

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Preparation of methyl 3-(benzyloxy)-5-((2,4-difluorobenzyl)carbamoyl)-


Provided herein is a process for preparing methyl 3-(benzyloxy)-5-((2,4- difluorobenzyl)carbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4- dihydropyridine-2-carboxylate, referred herein as Compound I.

Compound I may be used for preparing (4R,12aS)-N-(2,4-difluorobenzyl)- 7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H- pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide and salts thereof.

Example 1:

5-ethyl 2-methyl 3-(benzyloxy)-1-(2,2-dimethoxyethyl)-4-oxo-1,4- dihydropyridine-2,5-dicarboxylate (may be prepared according to the process disclosed in IP.COM 000238531D) (13.3 g) was dissolved in Toluene (100 mL). 2,4-difluorobenzylamine (4.22 mL) and acetic acid
(1.88 mL) were added and the reaction mixture was heated to 97°C and stirred for 12 hr. The reaction was monitored by HPLC and methyl 3- (benzyloxy)-5-((2,4-difluorobenzyl)carbamoyl)-1-(2,2-dimethoxyethyl)-4- oxo-1,4-dihydropyridine-2-carboxylate was obtained.