6-(prop-2-enoylamino)hexanoic acid

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

Procedure: To a solution of 6-Aminocaproic acid (10.0 g) in a 1.27 M aqueous sodium hydroxide solution (60 ml) was added a solution of acryloyl chloride (7.8 ml) in tetrahydrofuran (20 ml) dropwisely while chilling in ice water. During the addition, the reaction mixture was adjusted to be pH 8 to 9 by addition of 4 N aqueous sodium hydroxide solution. After the addition, the resulting mixture was stirred for 2 hours while being gradually cooled to room temperature. Subsequently, the reaction mixture was adjusted to be pH 3 by addition of 1 N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with distilled water and dried over anhydrous magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in a small amount of ethyl acetate and recrystallized from hexane to give the target compound (9.6 g). During the addition After the addition extracted with ethyl acetate The organic layer was washed with distilled water dried over anhydrous magnesium sulfate The magnesium sulfate was filtered off the filtrate was concentrated under reduced pressure The residue was dissolved in a small amount of ethyl acetate recrystallized from hexane

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

Procedure: Using the same procedure as previously described except substituting 6-aminocaproic acid for the glutamic acid, the crude product was obtained in greater than 85% yield. After crystallization from water or ethyl acetate, the white, crystalline N-acryloyl-6-aminocaproic acid had a melting point of 88°-90° C.

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

Procedure: N-acryloyl 2-glycine (A2AGA), N-acryloyl 4-aminobutyeric acid (A4ABA), N-acryloyl 6-aminocaproic acid (A6ACA) and N-acryloyl 8-aminocaprylic acid (A8ACA) were synthesized from glycine (Fisher Scientific Inc), 4-aminobutyeric acid, 6-aminocaproic acid and 8-aminocaprylic acid (Acros Organics Inc) respectively.

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

Procedure: N-acryloyl 2-glycine (A2AGA), N-acryloyl 4-aminobutyeric acid (A4ABA), N-acryloyl 6-aminocaproic acid (A6ACA) and N-acryloyl 8-aminocaprylic acid (A8ACA) were synthesized from glycine (Fisher Scientific Inc), 4-aminobutyeric acid, 6-aminocaproic acid and 8-aminocaprylic acid (Acros Organics Inc) respectively.

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

Procedure: Sodium hydroxide (7.6 g, 190 mmol) and 6-aminohexanoic acid (10 g, 76 mmol) were dissolved in distilled water (50 mL) at room temperature. Acryloyl chloride (8.24 g, 91 mmol) in dry CH2Cl2 (50 mL) was slowly added to the mixture at room temperature. The resulting mixture was stirred at room temperature for 10 h. The reaction was quenched by adding 10% HCl (20 mL, pH 3) at room temperature and the mixture was extracted with ethyl acetate (2×100 mL). The combined organic layers were dried over MgSO4 and concentrated to give a product as a white solid (11.6 g, 82%). This compound was used without further purification. The reaction was quenched by adding 10% HCl (20 mL, pH 3) at room temperature the mixture was extracted with ethyl acetate (2×100 mL) The combined organic layers were dried over MgSO4 concentrated

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

Procedure: To a solution of 6-Aminocaproic acid (10.0 g) in a 1.27 M aqueous sodium hydroxide solution (60 ml) was added a solution of acryloyl chloride (7.8 ml) in tetrahydrofuran (20 ml) dropwisely while chilling in ice water. During the addition, the reaction mixture was adjusted to be pH 8 to 9 by addition of 4 N aqueous sodium hydroxide solution. After the addition, the resulting mixture was stirred for 2 hours while being gradually cooled to room temperature. Subsequently, the reaction mixture was adjusted to be pH 3 by addition of 1 N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with distilled water and dried over anhydrous magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was dissolved in a small amount of ethyl acetate and recrystallized from hexane to give the target compound (9.6 g). During the addition After the addition extracted with ethyl acetate The organic layer was washed with distilled water dried over anhydrous magnesium sulfate The magnesium sulfate was filtered off the filtrate was concentrated under reduced pressure The residue was dissolved in a small amount of ethyl acetate recrystallized from hexane