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• W2986527858 abstract "An efficient process to synthesize Monobactam 1 from intermediates 2, 3, and 4 was developed. The process was initially enabled to deliver 500 g of 1 for exploratory toxicity studies and further improved to facilitate kilogram-scale production of the active pharmaceutical ingredient with enhanced quality and throughput. Highlights of the process encompass utilizing 1,1′-carbonyldiimidazole to construct a urea linker with good selectivity, oxidative cleavage to remove a 2,4-dimethoxybenzyl protecting group, two activation methods to form an amide bond, a high yielding reaction to introduce N-sulfonic moiety, and a global deprotection to remove all protecting groups. Practical procedures were developed to isolate intermediates en route by adding a concentrated substrate to antisolvents to obtain filterable amorphous solids with partial purification. Amberchrom CG161M resin was applied not only as a “resin-capture–release” tool to remove the bulk amount of water but also as an effective method to purify 1. Finally, a process isolating 1 pentahydrate (1·5H2O) as a crystalline solid from the acidic aqueous solution was developed based on zwitterionic crystallization methodology." @default.
• W2986527858 created "2019-11-22" @default.
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• W2986527858 date "2019-11-06" @default.
• W2986527858 modified "2023-09-27" @default.
• W2986527858 title "Enabled Process To Synthesize Monobactam <b>1</b> for Early Development" @default.
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• W2986527858 doi "https://doi.org/10.1021/acs.oprd.9b00374" @default.
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