Ch_322b_24.03

Ch_322b_24.03 - Synthesis of !-Amino Acids There are...

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Synthesis of ! -Amino Acids There are several standard syntheses of ! -amino acids. Direct Ammonolysis of ! -Halo Acids CH 3 CH 2 COOH (i) Br 2 , P (ii) H 2 O propanoic acid CH 3 CHCOOH Br 2-bromopropanoic acid excess NH 3 CH 3 CHCO 2 NH 3 + - alanine (as a racemic form)
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The Malonic Ester Synthetic Route COOEt CH 2 COOEt diethyl malonate (i) NaOEt, EtOH (ii) C 6 H 5 CH 2 Cl COOEt CH- CH 2 C 6 H 5 COOEt (i) HO - , H 2 O (ii) H 3 O + COOH CHCH 2 C 6 H 5 COOH Br 2 ether, heat COOH Br -CCH 2 C 6 H 5 COOH bromination occurs via the enol of the acid: C=C CH 2 C 6 H 5 COOH HO : HO heat, >100 o C (-CO 2 ) C 6 H 5 CH 2 CHCOOH Br excess NH 3 C 6 H 5 CH 2 CHCO 2 - NH 3 + phenylalanine (as a racemic form)
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The Gabriel Synthesis: Potassium Phthalimide ClCH 2 COOEt alkylation (i) KOH, H 2 O hydrolysis (ii) HCl neutralization COOH COOH phthalic acid + H 3 NCH 2 CO 2 - + glycine N H O O phthalimide (pK a = 8.3) KOBu-t N - O K + potassium phthalimide O N CH 2 COOEt O (97%) O
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Ch_322b_24.03 - Synthesis of !-Amino Acids There are...

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