Category: 57561-39-4

A common heterocyclic compound, 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, molecular formula is C8H17NO3, 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. 57561-39-4.

A solution of tert-butyl (2-hydroxyethyl)(methyl)carbamate (6.0 g, 34.24 mmol) and triethylamine (6.92 g, 68.48 mmol) in dichloromethane (100 mL) was added dropwise methanesulfonyl chloride (4.68 g, 41.09 mmol) at 0 oC under nitrogen. The reaction was stirred for 1 h at 0 oC. The resulting solution was washed with water (3×20 mL). The organic phase was dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under vacuum to afford 2-[tert-butoxycarbonyl(methyl)amino]ethyl methanesulfonate (8 g, 31.58 mmol, 92.2% yield) as a colorless oil. LCMS (ESI) [M+H]+ =254.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (2-hydroxyethyl)(methyl)carbamate, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; LIANG, Jun; MALHOTRA, Sushant; MENDONCA, Rohan V.; RAJAPAKSA, Naomi; SIU, Michael; STIVALA, Craig; TELLIS, John C.; WEI, BinQing; CHAN, Bryan K.; DROBNICK, Joy Alison; GAZZARD, Lewis J.; HEFFRON, Timothy; JONES, Graham; LAINCHBURY, Michael; MADIN, Andrew; SEWARD, Eileen; CARTWRIGHT, Matthew W.; GANCIA, Emanuela; FAVOR, David; FONG, Kin-Chiu; GOOD, Andrew; HU, Yonghan; (298 pag.)WO2020/23560; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

57561-39-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 57561-39-4 name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of tert-butyl (2-hydroxyethyl)(methyl)carbamate (1.0 g, 5.71 mmol) and triethylamine (1.15 g, 11.41 mmol) in dichloromethane (20 mL) was added dropwise methanesulfonyl chloride (975.86 mg, 8.56 mmol). The mixture was stirred at 0 C. for 1 hour. The resulting solution was washed with water and the organic phase was dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under vacuum to afford 2-[tert-butoxycarbonyl(methyl)amino]ethyl methanesulfonate (1.29 g, 5.08 mmol) as a colorless oil. LCMS (ESI) [M+H]+=254

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (2-hydroxyethyl)(methyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

57561-39-4, These common heterocyclic compound, 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)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.

2-(Boc-methyl-amino)-ethanol (0.19 g, 1 mmol) was dissolved in 4 mL of dichloromethane, and added with Dess-Martin periodinane (0.64 g, 1.5 mmol), and stirred at room temperature for 1 hour. 3 mL of a saturated sodium thiosulfate solution and 5 mL of a saturated sodium bicarbonate solution were added to the reaction mixture, and the mixture was stirred until clarified. Then, it was extracted with 20 mL of dichloromethane, and the dichloromethane layer was concentrated under reduced pressure. The residues were dissolved in 5 mL of acetic acid, and added with ethyl 5-bromo-3-amino-2-methyl-benzoate 1c (0.26 g, 1 mmol). The sodium borohydride (0.22 g, 6 mmol) was added portionwise and then stirred at room temperature for 0.5 hour. The reaction solution was added with water and ethyl acetate. The ethyl acetate layer was washed with aqueous solution of sodium hydroxide. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residues were purified by column chromatography (eluent: petroleum ether:ethyl acetate 30:1 to 3:1) to give 0.3 g of title product.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 57561-39-4.

Reference:
Patent; ANCUREALL PHARMACEUTICAL (SHANGHAI) CO., LTD.; Si, Jutong; Wang, Guan; Jiang, Meifeng; YANG, Zhihe; Zhou, Chentao; (118 pag.)US2019/345139; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics