Reaktion #467975

Reaktionsgleichung

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

Ausbeute 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

Ausbeute 61.8%

Lösungsmittel

tetrahydrofuran

methylene chloride

diethyl ether

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle