Coumarin-6-carboxylicacid

A mixture of 6-methyl coumarin (25 g, 0.156 mol) and chlorobenzene (25 ml) were added dropwise to a solution of 62.5percent sulfuric acid (152 ml) (35 g, 0.4026 mol) was added dropwise, and 62.5percent sulfuric acid (20 ml) was added dropwise. The reaction was carried out at 80-90 ° C for 1 h. After completion of the reaction, the system was cooled to room temperature and water (150 ml) was added. 25percent aqueous ammonia (43 ml) was added dropwise to the ice bath and then EtOAc (50 ml) and butanone (100 ml) were added, (2 x 20 ml), the organic layer was combined and the ketone was removed by steaming. To the system was added DMSO (15 ml), HCl (10 ml) and the residue was added to the reaction mixture. (8 ml) and 25percent sodium chlorite (55 ml) was added dropwise at 15-40 ° C. The mixture was stirred at this temperature for 30 min and stirred at 74-80 ° C for 15 min. After completion of the reaction, the mixture was cooled to room temperature and the organic layer was separated. Water (125 ml) was added to the organic layer, 25percent aqueous ammonia (20 ml) was added dropwise at 30-40 ° C, the pH of the solution reached 10, and the aqueous layer was separated. To the aqueous layer was added DMSO (70 ml), HCl (16 ml) was added dropwise at 30-40 ° C and the temperature was raised to 65-75 ° C by adding HCl (15 ml) dropwise. The mixture was stirred at the same temperature for 30 min, To give 14.8 g of a yellow solid in 50percent yield.Preparation of Compound 45, 2-oxo-2H-chromene-6-carboxylic acidMention may be made most particularly, alone or as a mixture, of the following lactones: ... 1, 3-dihydro-1-oxo-5-isobenzofurancarboxylic acid hexahydro-2-oxo-3, 5-methano-2H-cyclopenta[b]furan-7-carboxylic acid 6-methyl-2, 4-dioxo-2H-pyran-5-carboxylic acid 1-oxo-3-isochromancarboxylic acid 2-oxo-2H-1-benzopyran-6-carboxylic acid 6-methyl-2-oxo-2H-1-benzopyran-3-carboxylic acid 2, 5-dihydro-4, 5, 5-trimethyl-2-oxo-3-furancarboxylic acid tetrahydro-5-oxo-2-phenyl-3-furancarboxylic acid ...General procedure: N-(3-Dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (EDCI, 0.029g, 0.15mmol) and 1-hydroxybenzotriazole (HOBt, 0.015g, 0.11mmol) were sequentially added in batches to a stirring solution of General procedure: N-(3-Dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (EDCI, 0.029g, 0.15mmol) and 1-hydroxybenzotriazole (HOBt, 0.015g, 0.11mmol) were sequentially added in batches to a stirring solution of (raw material 10, 0.10 mmol)And N-[(2R, 3S)-2-hydroxy-3-amino-4-phenylbutane]-N-isobutyl-4-methoxybenzenesulfonamide (Intermediate III1a, 0.10 mmol) 2mL anhydrous DMF, cooling to 0 C, Slowly adding 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride under argon protection(EDCl, 0.15 mmol), 1-hydroxybenzotriazole (HOBt, 0.11 mmol), Stirring was continued for 10 min at 0 C, then transferred to room temperature for 1 h.4-Dimethylaminopyridine (DMAP, 0.020 mmol) was added and the reaction was continued for 2 h.The solvent was evaporated under reduced pressure, and then 4 mL water was evaporated, The organic phases were combined, dried over anhydrous Na 2 SO 4 and concentrated.Separation and purification by silica gel column chromatography (the eluent used is a mixture of petroleum ether and ethyl acetate in a mass ratio of 1:1 to 2:3), Obtained a pale yellow crystalline powder, That is, Compound 1 (0.050.g, 87%).N-(3-Dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (EDCI, 0.029g, 0.15mmol) and 1-hydroxybenzotriazole (HOBt, 0.015g, 0.11mmol) were sequentially added in batches to a stirring solution of Weigh 0.81g A mixture of Example 308A (75 mg, 0.164 mmol), A mixture of Example 308 A (75 mg, 0.164 mrnol),

Molecular Weight:190.15
XLogP3:0.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:190.02660867
Monoisotopic Mass:190.02660867
Topological Polar Surface Area:63.6
Heavy Atom Count:14
Complexity:295
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes