- Coh Coh 1 H2s Na Meoh 0 C To R T 2 H20 90 C 75 Coh A 72 80 Acz0 60 C 75 Hn Hs Hn Nh2 Valine B D Modified E 1 (39.04 KiB) Viewed 43 times
Draw the mechanism, using the specific compound. No “R” groups.
Indicate the type of reaction, such as nucleophilic acyl substitution, and the parts of the reaction, identifying the leaving group, the nucleophile, etc.
Provide the overall reaction sequence that involves your 5 reactions
COH COH 1. H2S, Na, MeOH 0°C to r.t. 2. H20,90 °C 75% COH A 72-80% Acz0, 60°C 75% HN HS HN NH2 (+)-Valine B D modified Erlenmeyer-Plochi azlactone synthesis 1.HCI, H20, A 2. acetone quant HO 2 M HCI brucine, H,0 then HCI sto NH, HCI SH HCO,H, Ac20 74% 99% COH "COH N "CO,H CHO F CHO rac-F G ÇOCH Buo, COM 1, N2H4 HO, H2O 1,4-dioxane, 13 °C tort 2. conc HCI, ACOH 13 °C tort 82% G. NaOAC3H20 EtOH-H,0 (1:1) 24% + 30% ep.1 -Buo, HN 1.Buo, HN PhthN H PhthN н HCI HN H H 1 vec CI K 1. K, EN, CH2Cl2 0°C tort Pho 2. HCI, CH2Cl2 56% 0 to 5 °C 3. pyridine acetone-H,0 (1:2) ÇOH KOH then DCC HN 1,4-dioxane-H2O (5:2) HOC 10-12% ÇOK NHH Pho H (+)-Penicillin V potassium salt V Pho L