ChemicalBook CAS DataBase List 1-N-Boc-3-Azetidinecarboxylic acid

1-N-Boc-3-Azetidinecarboxylic acid synthesis

6synthesis methods

Product Name:1-N-Boc-3-Azetidinecarboxylic acid
CAS Number:142253-55-2
Molecular formula:C9H15NO4
Molecular Weight:201.22

24424-99-5

36476-78-5

142253-55-2

General procedure for the synthesis of 1-Boc-azetidine-3-carboxylic acid from di-tert-butyl dicarbonate and 3-acridinecarboxylic acid: Example 4 Synthesis of 6-(3-{[(benzylsulfonyl)amino]carbonyl}azetidin-1-yl)-5-cyano-2-(difluoromethyl)nicotinate (a) Preparation of ethyl 1-(tert-butoxycarbonyl)azetidine-3-carboxylate Di-tert-butyl dicarbonate (25.535 g, 117 mmol) dissolved in methanol (70 mL) was added dropwise to a stirred solution of azetidine-3-carboxylic acid (10.11 g, 100 mmol) and triethylamine (27.8 mL, 200 mmol) in methanol (105 mL) over a period of 20 min. The reaction was carried out at room temperature (mild exotherm was observed) with continuous stirring for 18 hours. Upon completion of the reaction, the mixture was evaporated to dryness, tetrahydrofuran (120 mL) was added and evaporated again to afford the crude 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid, which could be used in the next step without further purification. Yield: 25.89 g (128%). 1H NMR (400 MHz, CDCl3) δ 1.43 (9H, s), 3.21-3.34 (1H, m), 4.00-4.13 (4H, m).

24424-99-5 Synthesis

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

36476-78-5 Synthesis

36476-78-5
435 suppliers
$6.00/1g

142253-55-2
330 suppliers
$6.00/1g

Yield:142253-55-2 100%

Reaction Conditions:

with triethylamine in methanol at 20; for 18 h;

Steps:

4.a

Example 4Ethyl 6-(3-{[(benzylsuIfonyl)amino]carbonyl}azetidin-l-yl)-5-cyano-2- 30 (difluoromethyl)nicotinate(a) l-(tert-Butoxycarbonyl)azetidine-3-carboxylic acid 91(BoC)₂O (25.535 g, 117 mmol) dissolved in MeOH (70 mL) was added dropwise during 20 minutes to a stirred slurry of azetidine-3-carboxylic acid (10.11 g, 100 mmol) and Et₃N (27.8 mL, 200 mmol) in MeOH (105 mL) at r.t (mildly exotermic reaction) and the mixture 5 was stirred over night (18 hours). The reaction was evaporated to dryness and THF (120 mL) was added and evapoprated to give crude l-(tert-butoxycarbonyl)azetidine-3- carboxylic acid which was used without further purification in the next step. Yield: 25.89 g (128 %) ¹H NMR (400 MHz, CDCl₅) δ 1.43 (9H, s), 3.21-3.34 (IH, m), 4.00-4.13 (4H, m).10

References:

WO2008/4946,2008,A1 Location in patent:Page/Page column 90-91