Compound or salt thereof and preparation method and application of same
a technology of compound or salt, applied in the field of compound or salt thereof, can solve the problems of difficult modification, low yield, and difficult to synthesize polypeptide drugs
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example 1 preparation
of the Compound of Formula (xii)
[0143]The compound of Formula (xii) was prepared by the following route in this Example:
[0144](1) Preparation of Compound xii-1
[0145]4-methoxysalicylaldehyde (100 g, 657 mmol, 1.0 eq) and K2CO3 (181 g, 1314 mmol, 2.0 eq) were weighed and put in a 1 L reaction vessel, to which THF (3.0 eq, 300 ml) and ethyl 4-bromobutyrate (192 g (141 ml), 985.5 mmol, 1.5 eq) were added, followed by stirring and heating until the reaction was complete. Then post-treatment and MTBE recrystallization followed by drying were carried out to obtain compound A-2-1, 155 g in total (yield: 88.7%, purity: 98.67%).
[0146](2) Preparation of Compound xii-2
[0147]155 g of compound xii-1 was transferred to a 2 L reaction bottle, to which a solution of EtNH2.HCl (59.69 g, 732 mmol, 1.5 eq) and NaBH3CN (92.0 g, 1464 mmol, 3 eq) in MeOH was added, followed by stirring at room temperature for 24 hours. Then NaOH (48.8 g, 1220 mmol, 2.5 eq) was added, followed by stirring for 12 hours. The...
example 2 preparation
of the Compound of Formula (xii)
[0152](1) Preparation of Compound xii-1
[0153]4-methoxysalicylaldehyde (100 g, 657 mmol, 1.0 eq) and K2CO3 (181 g, 1314 mmol, 2.0 eq) were weighed and put in a 1 L reaction vessel, to which THF (3.0 eq, 300 ml) and ethyl 4-bromobutyrate (192 g (141 ml), 985.5 mmol, 1.5 eq) were added, followed by stirring and heating until the reaction was completed. Then post-treatment and MTBE recrystallization followed by drying were carried out to obtain compound xii-1, 159.3 g in total (yield: 89.8%, purity: 98.80%).
[0154](2) Preparation of Compound xii-2
[0155]To the above reaction vessel containing 159.3 g of compound A-2-1, an aqueous solution of NaOH (59.8 g, 1495 mmol, 2.5 eq) in methanol was added, and EtNH2.HCl (73.14 g, 897 mmol, 1.5 eq) and Pd / C (22.2 g) were finally added, followed by pressurization with H2 to 0.2˜20 bar and stirring at room temperature of 25° C. until the reaction was completed. After filtration, removal of Pd / C, and rotary drying of met...
example 3 preparation
of Compound of Formula xiii
[0160]
[0161](1) 4-methoxysalicylaldehyde (100 g, 657 mmol, 1.0 eq) and K2CO3 (181 g, 1314 mmol, 2.0 eq) were weighed and put in a 1 L reaction vessel, to which THF (3.0 eq, 300 ml) and ethyl 4-bromobutyrate (192 g (141 ml), 985.5 mmol, 1.5 eq) were added, followed by stirring and heating until the reaction was completed. Then post-treatment and MTBE recrystallization followed by drying were carried out to obtain compound xii-1, 154.6 g in total (yield: 87.0%, purity: 98.47%).
[0162](2) To the above reaction vessel containing 154.6 g compound xii-1, an aqueous solution of NaOH (58.1 g, 1451.5 mmol, 2.5 eq) in methanol was added, and EtNH2.HCl (71.0 g, 870.9 mmol, 1.5 eq) and Pd / C (22.5 g) were finally added, followed by pressurization with H2 to 0.2-20 bar and stirring at room temperature of 25° C. until the reaction was completed. After filtration, removal of Pd / C, and rotary drying of methanol, the residue was extracted with MTBE once and directly used for...
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