ChemicalBook CAS DataBase List Azetidine-1,2-dicarboxylic acid 1-tert-butyl ester

Azetidine-1,2-dicarboxylic acid 1-tert-butyl ester synthesis

4synthesis methods

Product Name:Azetidine-1,2-dicarboxylic acid 1-tert-butyl ester
CAS Number:159749-28-7
Molecular formula:C9H15NO4
Molecular Weight:201.22

Sodium hydroxide (2.08 g, 51.92 mmol) was added to a solution of azetidine-2-carboxylic acid (5.00 g, 49.50 mmol), di-tert-butyl dicarbonate (13.50 g, 61.80 mmol) in ethanol (120.0 mL) at 0 °C. After stirring the reaction mixture for 8 hours, the pH of the mixture was adjusted to 2 with 1.0 N HCl and extracted with ethyl acetate (2 × 200 mL). The combined organic layers were washed with brine, separated, and dried over anhydrous sodium sulfate. Then the compound was concentrated under reduced pressure to afford Azetidine-1,2-dicarboxylic acid 1-tert-butyl ester.

AZETIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER

24424-99-5 Synthesis

24424-99-5
835 suppliers
$13.50/25G

2517-04-6 Synthesis

2517-04-6
110 suppliers
$5.00/50mg

159749-28-7
145 suppliers
$9.00/250mg

Yield:159749-28-7 74.6%

Reaction Conditions:

with water;sodium hydroxide in ethanol at 0 - 20; for 8 h;

Steps:

27.1 Step 1. Synthesis of 1-(tert-butoxycarbonyl) azetidine-2-carboxylic acid

To a solution of azetidine-2-carboxylic acid (5.00 g, 49.50 mmol), di-tert-butyl dicarbonate (13.50 g, 61.80 mmol) in ethanol (120.0 mL) was added the solution of sodium hydroxide (2.08 g, 51.92 mmol) in H2O (40.0 mL) at 0 °C. After stirring the reaction mixture at rt for 8 hours, the pH of the mixture was adjusted to pH 2 with 1.0 N HCl and extracted with ethyl acetate (2 × 200 mL). The combined organic layers were washed with brine, separated and dried over anhydrous sodium sulfate, then concentrated under reduced pressure to afford 1-(tert-butoxycarbonyl) azetidine-2-carboxylic acid (7.43 g, 74.6%) as off-white solid.¹H NMR (500 MHz, CDCl₃) d 4.82-4.78 (m, 1H), 3.92-3.88 (m, 2H), 2.62-2.58 (m, 1H), 2.42-2.38 (m, 1H), 1.45 (s, 9H). MS (ESI) m/z: 202.1 (M+1)⁺.

References:

WO2021/46315,2021,A2 Location in patent:Page/Page column 43; 68

24424-99-5 Synthesis

24424-99-5
835 suppliers
$13.50/25G

7729-30-8 Synthesis