Industrial continuous preparing process of N-tert-butoxy carbonyl-5-aza-2-oxa-3-one-dicyclo-[2,2,1] heptane
A technology of tert-butoxycarbonyl and oxa, applied to the industrialization of continuous synthesis of N-tert-butoxycarbonyl-5-aza-2-oxa-3-one-bicyclo-[2,2,1]heptane In the field of preparation, it can solve the problems of inability to scale production and achieve the effects of easy reaction, low preparation cost and reasonable choice of reaction process
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Embodiment 1
[0034] Synthesis of N-tert-butoxycarbonyl-5-aza-2-oxa-3-one-bicyclo-[2,2,1]heptane
[0035] The first step: Synthesis of N-tert-butoxycarbonyl-O-p-toluenesulfonyl-L-hydroxyproline methyl ester
[0036] L-hydroxyproline (300g, 2.29mol) was dissolved in anhydrous methanol (2.0L), and thionyl chloride (335g, 2.8mol) was added dropwise at room temperature, and the reaction solution was refluxed and stirred for 1 hour, and concentrated to dryness to obtain a crude product L-hydroxyproline methyl ester hydrochloride is directly dissolved in methanol (6.0L), and triethylamine (680g, 6.3mol) and BOC anhydride (520g, 2.4mol) are added at room temperature, and after 1 hour of reaction, Concentrate to dryness to obtain the crude product N-tert-butoxycarbonyl-L-hydroxyproline methyl ester, which is dissolved in dichloromethane (3L), and anhydrous pyridine (237g, 3.0mol) and p-toluenesulfonyl chloride are added at room temperature (437g, 2.3mol), reacted for 2 hours, added saturated a...
Embodiment 2
[0040] Synthesis of N-tert-butoxycarbonyl-5-aza-2-oxa-3-one-bicyclo-[2,2,1]heptane
[0041] The first step: Synthesis of N-tert-butoxycarbonyl-O-p-toluenesulfonyl-L-hydroxyproline methyl ester
[0042]L-hydroxyproline (72g, 0.55mol) was dissolved in anhydrous methanol (0.48L), concentrated sulfuric acid (60g, 0.6mol) was added dropwise at room temperature, the reaction solution was stirred at room temperature for 5 hours, and concentrated to dryness to obtain the crude product L- Hydroxyproline methyl ester hydrochloride, directly dissolve it in methanol (1.44L), add triethylamine (163g, 1.5mol) and BOC anhydride (1245g, 0.58mol) at room temperature, react for 1 hour, and concentrate to dryness , to obtain the crude product N-tert-butoxycarbonyl-L-hydroxyproline methyl ester, which was dissolved in toluene (0.72L), and anhydrous pyridine (56.9g, 0.72mol) and p-toluenesulfonyl chloride (104g , 0.55mol), reacted for 2 hours, added saturated aqueous sodium bicarbonate (0.72L...
Embodiment 3
[0046] Synthesis of N-tert-butoxycarbonyl-5-aza-2-oxa-3-one-bicyclo-[2,2,1]heptane
[0047] The first step: Synthesis of N-tert-butoxycarbonyl-O-p-toluenesulfonyl-L-hydroxyproline methyl ester
[0048] L-hydroxyproline (3g, 22.9mmol) was dissolved in anhydrous methanol (20mL), acetyl chloride (2.2g, 28mmol) was added dropwise at room temperature, the reaction solution was stirred at reflux for 1 hour, and concentrated to dryness to obtain the crude product L-hydroxyproline Proline methyl ester hydrochloride, directly dissolve it in 1,4-dioxane (60mL), add triethylamine (6.8g, 63mmol) and BOC anhydride (5.2g, 24mmol) at room temperature, reaction 1 After one hour, it was concentrated to dryness to obtain the crude product N-tert-butoxycarbonyl-L-hydroxyproline methyl ester, which was dissolved in tetrahydrofuran (30mL), and anhydrous triethylamine (3.0g, 30mol) was added at room temperature and p- Toluenesulfonyl chloride (4.4g, 23mmol), reacted for 2 hours, added saturate...
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