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ID: 527108 • Letter: H
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https://s3.amazonaws.com/iedu attachments lesson/3e19da73809ef81 db99ccf26c17be7 p OH OH NH 1. TFA, MsOH 2. CDI HCI CO2Me Ns HO 3. NaOH nt of a practical asymmetric synthesis of a glucagon receptor antagonist drug or the treatment of type 2 diabetes is described. The antagonist consists of a 1,1,2,2 uted ethane core substituted with a propyl and three aryl groups including a fluoro- key steps to construct the ethane core and the two stereogenic centers involved a tion, an asymmetric hydrogenation via dynamic kinetic resolution, and an antiExplanation / Answer
The starting materials are 4- methyl 7- fluoro N(2 nitro sulphonyl) indole and 1-(4- chlorophenyl) 2- ( 4 carboxy phenyl)1-pentanol choral molecule
The ending materials are indole substituted amido carboxylic acid.
This reaction has two parts,
1. The reaction of alcohol with MsOH in presence of TFA to protonate and loosing the protonated hydroxyl group leading to a stable carbocation which is benzylic being stabilised by aromatic ring. The indole molecule has the partially electron rich C3 carbon forms an intermediate leading to the first intermediate.
2. This intermediate reacts with zCDI to form an activated ester which will reacts with amino ester hydrochloride yielding the corresponding amido acid.
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