반응 #46281

반응 방정식

tert-butyl bromoacetate

6-(3-chloro-4-fluorobenzyl)-3,4-dihydroxy-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide

magnesium methoxide

→

title compound

Methyl 2-(2-tert-butoxy-2-oxoethyl)-6-(3-chloro-4-fluorobenzyl)-4-hydroxy-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate

용매

ethyl acetate

DMSO

methanol

DMSO

반응 조건

후처리

1. 1
   기타Methanol was exhaustively removed under vacuum over 45 minutes
2. 2
   세척washed with ice cold dilute hydrochloric acid
3. 3
   추출The organic extract
4. 4
   세척was washed with aqueous sodium thiosulfate, brine
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated under vacuum
8. 8
   기타The residue was triturated with a mixture of diethyl ether and ethyl acetate
9. 9
   기타The solid precipitated
10. 10
    여과was collected by filtration

실험 절차

A mixture of 6-(3-chloro-4-fluorobenzyl)-3,4-dihydroxy-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide (0.50 g, 1.31 mmol; Example 1, Step 9) and magnesium methoxide in methanol (6.6 mL, 6-10% methanol solution available from Aldrich) in DMSO (13 mL) was heated at 60° C. for one hour. Methanol was exhaustively removed under vacuum over 45 minutes. The resultant DMSO solution was treated with tert-butyl bromoacetate (1.80 g, 10.50 mmol) and stirred at 50° C. under an atmosphere of nitrogen for one hour. The reaction mixture was diluted with ethyl acetate and washed with ice cold dilute hydrochloric acid. The organic extract was washed with aqueous sodium thiosulfate, brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was triturated with a mixture of diethyl ether and ethyl acetate. The solid precipitated was collected by filtration to provide the title compound. ES MS M+1=495

출처