(Z)-3-(furan-2-yl)prop-2-enoyl chloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 75 ml of water was suspended 6.5 g of DL-glutamic acid, and 5.2 g of sodium hydroxide was added, after which the resulting mixture was cooled to -10° C. to -7° C., and a solution of 6 g of β-(2-furyl)acrylic acid chloride in 75 ml of diethyl ether was added thereto dropwise over a period of 1 hour. After the addition, the mixture thus obtained was subjected to reaction at the same temperature for 5 hours, after which the aqueous layer was separated and then adjusted to pH 5.5 with diluted hydrochloric acid. The aqueous layer was washed with two 50-ml portions of ethyl acetate, and the aqueous layer was separated. This aqueous layer was adjusted to pH 2 with diluted hydrochloric acid and then extracted with 100 ml of ethyl acetate, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure to obtain 5.5 g (yield 52%) of DL-N-[β-(2-furyl)acryloyl]glutamic acid having a melting point of 174.5°-175.5° C. was added after which the resulting mixture was cooled to -10° C. to -7° C. After the addition the mixture thus obtained was subjected to reaction at the same temperature for 5 hours after which the aqueous layer was separated The aqueous layer was washed with two 50-ml portions of ethyl acetate the aqueous layer was separated extracted with 100 ml of ethyl acetate the organic layer was separated The organic layer was dried over anhydrous magnesium sulfate the solvent was removed by distillation under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 75 ml of water was suspended 6.5 g of DL-glutamic acid, and 5.2 g of sodium hydroxide was added, after which the resulting mixture was cooled to -10° C. to -7° C., and a solution of 6 g of β-(2-furyl)acrylic acid chloride in 75 ml of diethyl ether was added thereto dropwise over a period of 1 hour. After the addition, the mixture thus obtained was subjected to reaction at the same temperature for 5 hours, after which the aqueous layer was separated and then adjusted to pH 5.5 with diluted hydrochloric acid. The aqueous layer was washed with two 50-ml portions of ethyl acetate, and the aqueous layer was separated. This aqueous layer was adjusted to pH 2 with diluted hydrochloric acid and then extracted with 100 ml of ethyl acetate, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure to obtain 5.5 g (yield 52%) of DL-N-[β-(2-furyl)acryloyl]glutamic acid having a melting point of 174.5°-175.5° C. was added after which the resulting mixture was cooled to -10° C. to -7° C. After the addition the mixture thus obtained was subjected to reaction at the same temperature for 5 hours after which the aqueous layer was separated The aqueous layer was washed with two 50-ml portions of ethyl acetate the aqueous layer was separated extracted with 100 ml of ethyl acetate the organic layer was separated The organic layer was dried over anhydrous magnesium sulfate the solvent was removed by distillation under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a homogeneous solution of 15.6 g. (80 mM) of piperazine hexahydrate and 13.8 g. (80 mM) of 47% hydrobromic acid in 40 ml. of ethanol there were added dropwise at room temperature another solution of 6.3 g. (40 mM) of 3-(Furan-2-yl)-acryloylchloride in 10 ml. of tetrahydrofuran. After stirring for two hours at room temperature, the resulting solution was heated at 80° for two hours. Then the solution was cooled with ice and the forming crystals of piperazine hydrobromide were filtered off. The filtrate was condensed under reduced pressure and 80 ml. of 2 N-hydrochloric acid was added into the residue. After neutral substances were removed by extraction with ethyl acetate, the resulting solution was made alkaline with 5 N sodium hydroxide and extracted again with ethyl acetate. After drying over anhydrous sulfate, the combined extracts were condensed to give 4.62 g. of 3-(Furan-2-yl)-acryloylpiperazine (56% yield). the resulting solution was heated at 80° for two hours Then the solution was cooled with ice the forming crystals of piperazine hydrobromide were filtered off condensed under reduced pressure and 80 ml After neutral substances were removed by extraction with ethyl acetate extracted again with ethyl acetate After drying over anhydrous sulfate condensed to give 4.62 g

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 75 ml of water was suspended 6.5 g of DL-glutamic acid, and 5.2 g of sodium hydroxide was added, after which the resulting mixture was cooled to -10° C. to -7° C., and a solution of 6 g of β-(2-furyl)acrylic acid chloride in 75 ml of diethyl ether was added thereto dropwise over a period of 1 hour. After the addition, the mixture thus obtained was subjected to reaction at the same temperature for 5 hours, after which the aqueous layer was separated and then adjusted to pH 5.5 with diluted hydrochloric acid. The aqueous layer was washed with two 50-ml portions of ethyl acetate, and the aqueous layer was separated. This aqueous layer was adjusted to pH 2 with diluted hydrochloric acid and then extracted with 100 ml of ethyl acetate, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure to obtain 5.5 g (yield 52%) of DL-N-[β-(2-furyl)acryloyl]glutamic acid having a melting point of 174.5°-175.5° C. was added after which the resulting mixture was cooled to -10° C. to -7° C. After the addition the mixture thus obtained was subjected to reaction at the same temperature for 5 hours after which the aqueous layer was separated The aqueous layer was washed with two 50-ml portions of ethyl acetate the aqueous layer was separated extracted with 100 ml of ethyl acetate the organic layer was separated The organic layer was dried over anhydrous magnesium sulfate the solvent was removed by distillation under reduced pressure