Synthetic Route of 152120-54-2, These common heterocyclic compound, 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
A solution of (1S,2R)-1-((2R,3R,4S)-3-acetamido-4-azido-6-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate (5.1 g, 11.5 mmol) in ethanol (300 mL) was hydrogenated with Lindlar’s catalyst for 8 h (1 atmospheric pressure). The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in THF (50 mL). This solution was mixed with tert-butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate (13.1 g, 42.21 mmol) and the resulting reaction mixture was stirred at room temperature for 18 h. It was then diluted with aq. NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Purification by silica gel chromatography (gradient elution, 1:1 EtOAc/pentane to 100% EtOAc) to afford 4.0 g of (1S,2R)-1-((2R,3R,4S)-3-acetamido-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-6-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate (50%). (1S,2R)-1-((2R,3R,4S)-3-Acetamido-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-6-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate (4.0 g, 5.94 mmol) was dissolved in methanol (20 mL) and treated with 1N NaOH (6 mL) with cooling in an ice-bath. The reaction was stirred for 30 min and neutralized with 1N HCl. Then the reaction was concentrated under reduced pressure and the residue was re-dissolved in methanol and filtered. The filtrate was concentrated under reduced pressure to afford 3.0 g of (2R,3R,4S)-3-acetamido-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-((1S,2R)-1,2,3-triacetoxypropyl)-3,4-dihydro-2H-pyran-6-carboxylic acid (95%).
The synthetic route of 152120-54-2 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Catabasis Pharmaceuticals, Inc.; Milne, Jill C.; Jirousek, Michael R.; Vu, Chi B.; Wensley, Allison; Ting, Amal; (180 pag.)US2016/129122; (2016); A1;,
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