sodium;thiobenzate

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

Procedure: 155 g of L-histidine and 189 g of sodium hydrogen carbonate were dissolved in 1 liter of water and 124 g of chloroacetyl chloride was added dropwise to the resulting solution with stirring and ice-cooling. After allowing the reaction to proceed for 1 hour, an aqueous solution of sodium thiobenzoate which was prepared from 152 g of thiobenzoic acid and 220 ml of 5 N solution of sodium hydroxide solution, was added dropwise to the resulting solution and was kept standing overnight at room temperature to allow reaction. The resulting reation solution was acidified with hydrochloric acid with ice-cooling to precipitate crystals. The crystals were collected on the filter and washed with water. The product thus obtained weighed 140 g (42 percent of the theoretical amount). Recrystallization from water gave colorless needles, m.p. 176°-177° C. ice-cooling the reaction was added dropwise to the resulting solution was kept standing overnight at room temperature reaction cooling to precipitate crystals The crystals were collected on the filter washed with water The product thus obtained Recrystallization from water gave colorless needles, m.p. 176°-177° C.

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

Procedure: As for Example 1, the preceding compound is coupled to L-proline to give 1-[3-(1-methyl-2-pyrrolylcarbonyl)propionyl]-L-proline. The preceding compound (0.01 mole) is brominated with bromine (0.011 mole) in acetic acid and the resulting 1-[3-bromo-(1-methyl-2-pyrrolylcarbonyl)propionyl]-L-proline (0.01 mole) is reacted with sodium thiobenzoate as for Example 21 to give the product of the Example as a glass. to give the product of the Example as a glass

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

Procedure: As for Example 21, 0.01 mole of 1-[3-bromo-3-(5-chloro-2-thenoyl)propionyl]-L-proline is reacted with sodium thiobenzoate for 16 hours in acetonitrile to give the product of the Example as a glass. to give the product of the Example as a glass

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

Procedure: As for Example 1, the preceding compound is coupled to L-proline to give 1-[3-(1-methyl-2-pyrrolylcarbonyl)propionyl]-L-proline. The preceding compound (0.01 mole) is brominated with bromine (0.011 mole) in acetic acid and the resulting 1-[3-bromo-(1-methyl-2-pyrrolylcarbonyl)propionyl]-L-proline (0.01 mole) is reacted with sodium thiobenzoate as for Example 21 to give the product of the Example as a glass. to give the product of the Example as a glass

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

Procedure: As for Example 21, 0.01 mole of 1-[3-bromo-3-(5-chloro-2-thenoyl)propionyl]-L-proline is reacted with sodium thiobenzoate for 16 hours in acetonitrile to give the product of the Example as a glass. to give the product of the Example as a glass

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

Procedure: As for Example 1, the preceding compound is coupled to L-proline to give 1-[3-(1-methyl-2-pyrrolylcarbonyl)propionyl]-L-proline. The preceding compound (0.01 mole) is brominated with bromine (0.011 mole) in acetic acid and the resulting 1-[3-bromo-(1-methyl-2-pyrrolylcarbonyl)propionyl]-L-proline (0.01 mole) is reacted with sodium thiobenzoate as for Example 21 to give the product of the Example as a glass. to give the product of the Example as a glass

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

Procedure: As for Example 21, 0.01 mole of 1-[3-bromo-3-(5-chloro-2-thenoyl)propionyl]-L-proline is reacted with sodium thiobenzoate for 16 hours in acetonitrile to give the product of the Example as a glass. to give the product of the Example as a glass

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

Procedure: 155 g of L-histidine and 189 g of sodium hydrogen carbonate were dissolved in 1 liter of water and 124 g of chloroacetyl chloride was added dropwise to the resulting solution with stirring and ice-cooling. After allowing the reaction to proceed for 1 hour, an aqueous solution of sodium thiobenzoate which was prepared from 152 g of thiobenzoic acid and 220 ml of 5 N solution of sodium hydroxide solution, was added dropwise to the resulting solution and was kept standing overnight at room temperature to allow reaction. The resulting reation solution was acidified with hydrochloric acid with ice-cooling to precipitate crystals. The crystals were collected on the filter and washed with water. The product thus obtained weighed 140 g (42 percent of the theoretical amount). Recrystallization from water gave colorless needles, m.p. 176°-177° C. ice-cooling the reaction was added dropwise to the resulting solution was kept standing overnight at room temperature reaction cooling to precipitate crystals The crystals were collected on the filter washed with water The product thus obtained Recrystallization from water gave colorless needles, m.p. 176°-177° C.

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

Procedure: As for Example 1, the preceding compound is coupled to L-proline to give 1-[3-(1-methyl-2-pyrrolylcarbonyl)propionyl]-L-proline. The preceding compound (0.01 mole) is brominated with bromine (0.011 mole) in acetic acid and the resulting 1-[3-bromo-(1-methyl-2-pyrrolylcarbonyl)propionyl]-L-proline (0.01 mole) is reacted with sodium thiobenzoate as for Example 21 to give the product of the Example as a glass. to give the product of the Example as a glass

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

Procedure: As for Example 21, 0.01 mole of 1-[3-bromo-3-(5-chloro-2-thenoyl)propionyl]-L-proline is reacted with sodium thiobenzoate for 16 hours in acetonitrile to give the product of the Example as a glass. to give the product of the Example as a glass

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

Procedure: As for Example 1, the preceding compound is coupled to L-proline to give 1-[3-(1-methyl-2-pyrrolylcarbonyl)propionyl]-L-proline. The preceding compound (0.01 mole) is brominated with bromine (0.011 mole) in acetic acid and the resulting 1-[3-bromo-(1-methyl-2-pyrrolylcarbonyl)propionyl]-L-proline (0.01 mole) is reacted with sodium thiobenzoate as for Example 21 to give the product of the Example as a glass. to give the product of the Example as a glass

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

Procedure: As for Example 21, 0.01 mole of 1-[3-bromo-3-(5-chloro-2-thenoyl)propionyl]-L-proline is reacted with sodium thiobenzoate for 16 hours in acetonitrile to give the product of the Example as a glass. to give the product of the Example as a glass