ChemicalBook CAS DataBase List N-Boc-4-oxo-L-proline

N-Boc-4-oxo-L-proline synthesis

9synthesis methods

Product Name:N-Boc-4-oxo-L-proline
CAS Number:84348-37-8
Molecular formula:C10H15NO5
Molecular Weight:229.23

13726-69-7
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84348-37-8
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$5.00/250mg

Yield:84348-37-8 95.9%

Reaction Conditions:

with 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical;trichloroisocyanuric acid in ethyl acetate at -5 - 30; for 1.33333 h;

Steps:

2 Example 2: Preparation of 1-(tert-butoxycarbonyl)-4-oxo-L-proline (Formula V)

Trichloroisocyanuric acid (75.6 g) was added to a solution of (4R)-1-(tert- butoxycarbonyl)-4-hydroxy-L-proline (Formula IV, prepared according to the process of Example 1; 100 g) in ethyl acetate (1000 mL). The solution was cooled to 0°C to -5°C. A solution of TEMPO in ethyl acetate (3.38 g in 50 mL ethyl acetate) was slowly added to the reaction mixture at -5°C to 10°C, and the reaction mixture was stirred at the same temperature for 20 minutes. The reaction mixture was heated to a temperature of 25°C to 30°C, and stirred at the same temperature for 60 minutes. After completion of the reaction, the reaction mixture was quenched with deionized water (200 mL), and stirred for 60 minutes at a temperature of about 25°C to 30°C. The reaction mixture was filtered through a Hyflo bed. The filtrate was washed with deionized water (2 x 200 mL). The layers were separated. The organic layer was washed with an aqueous solution of sodium chloride (prepared by adding 40 g sodium hydroxide to 200 mL deionized water). The organic layer was concentrated at a temperature of about 50°C under reduced pressure to obtain a residue. The residue was dissolved in ethyl acetate ( 100 mL). Hexanes (400 mL) were slowly added to the solution of ethyl acetate. The reaction mixture was stirred at 25°C to 30°C for 30 minutes. The reaction mixture was filtered to obtain a solid. The solid was washed with a mixture of ethyl acetate (20 mL) and hexanes (80 mL), and dried at 40°C to 45°C under reduced pressure to obtain 1-(tert-butoxycarbonyl)-4-oxo-L-proline. Yield: 95.9%

References:

WO2015/19238,2015,A1 Location in patent:Page/Page column 9

24424-99-5 Synthesis