반응 #467975

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methyl bromoacetate

2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl isothiocyanate

N,N-diisopropylethylamine

L-phenylalanine, methyl ester, hydrochloride

→

title product

수율 61.8%

Methyl α-benzyl-2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-primidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate

수율 61.8%

용매

tetrahydrofuran

methylene chloride

diethyl ether

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후처리

1. 1
   workup.STIRRINGshaken at 40° C. for 16 hours
2. 2
   농축concentrated in vacuo
3. 3
   기타to obtain a residue

실험 절차

A solution of 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl isothiocyanate (0.38 g, 1.0 mmol) and N,N-diisopropylethylamine (1.0 mL) in tetrahydrofuran is treated with L-phenylalanine, methyl ester, hydrochloride (0.18 g, 1.0 mmol), shaken at 40° C. for 1 hour, treated with methyl bromoacetate (0.46 g, 3.0 mmol), shaken at 40° C. for 16 hours, and concentrated in vacuo to obtain a residue. Column chromatography of the residue using silica gel and 0% to 10% diethyl ether in methylene chloride solutions gives the title product (0.37 g) which is identified by 1H and 13C NMR spectral analyses.

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