5-[(S)-2,2-Dimethyltetrahydro-2H-pyran-4-yl]-1-[(1S,2S)-2-methyl-1-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)cyclopropyl]-1H-indole-2-carboxylic Acid

China [CN]

Chinese Formal Name: 5-[(S)-2,2-Dimethyltetrahydro-2H-pyran-4-yl]-1-[(1S,2S)-2-methyl-1-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)cyclopropyl]-1H-indole-2-carboxylic acid

Molecular Formula (Derived): C₂₇H₂₉N₃O₅ (Derived from the structure: indole core + cyclopropyl group + tetrahydropyran group + 1,2,4-oxadiazolone ring + carboxyl group, containing 3 N and 5 O atoms)

Molecular Weight (Derived): 475.54 (Used for molar concentration calculations and product quantification, contains a polar carboxyl group, resulting in a higher molecular weight compared to earlier intermediates)

Core Use: A key carboxylic acid intermediate in the synthesis of Orforglipron API, acting as a carboxyl group donor to construct the amide bond framework of the final API through amidation condensation reaction.

Key Structural Features: 1. Contains a 1,2,4-oxadiazolone heterocycle (characteristic side chain of Orforglipron); 2. Terminal carboxyl group (-COOH) (active reaction site); 3. Multiple chiral centers + heterocyclic structure, moderate molecular polarity.

Related Synthesis Reaction: Obtained from a previous hydroxyimino methyl intermediate through cyclization reaction (to construct the oxadiazolone ring) + deamidation reaction (formamide → carboxylic acid).

Key Physicochemical Properties (Derived): 1. Acidity/Basicity: Contains a carboxyl group, weakly acidic, expected pKa of 3.5~4.5 (can form salts with bases, facilitating purification/dissolution); 2. Solubility: Slightly soluble in water, readily soluble in organic solvents such as methanol, dichloromethane, and DMF; 3. Melting Point: Expected 200~220℃ (heterocyclic + carboxylic acid structure, relatively high melting point).