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0 °C

A solution of diisopropylamine (8.4 mL) in tetrahydrofuran (100 mL) was cooled to -78° C. under argon and a solution of n-butyl lithium (30 mL of 2.5 M in hexane) was added. The mixture was stirred at -78° C. for 30 minutes and at 0°C. for 10 minutes. After being recooled to -78° C., a solution of N-(diphenylmethylene)-glycine ethyl ester (Tetra. Lett., (1978), 2541, 4625) (15.4 g) in tetrahydrofuran (50 mL) was added, the mixture was stirred for 1 hour at -78° C. and a solution of 1-(2-chlorophenyl)methyl-5-chloromethyl-2-propylthio-1H-imidazole hydrochloride (9.4 g) in dry dimethylformamide (20 mL) was added. The mixture was then stirred at ambient temperature for 18 hours, poured into saturated ammonium chloride solution and the aqueous layer was extracted with methylene chloride. The organic extracts were washed with water, dried with magnesium sulfate concentrated and chromatographed over silica gel with 1% methanol in methylene chloride to afford 6.88 g of 3-[(2-chlorophenyl)methyl]-2-propylthio-N-(diphenylmethylene)histidine ethyl ester.

1. customAfter being recooled to -78° C.
2. stirringthe mixture was stirred for 1 hour at -78° C.
3. stirringThe mixture was then stirred at ambient temperature for 18 hours
4. extractionthe aqueous layer was extracted with methylene chloride
5. washThe organic extracts were washed with water
6. dry with materialdried with magnesium sulfate
7. concentrationconcentrated
8. customchromatographed over silica gel with 1% methanol in methylene chloride