1-Boc-L-azetidine-2-carboxylic acid Chemical Properties

Melting point:

105-110 °C

Boiling point:

339.14°C (rough estimate)

Density 

1.2250 (rough estimate)

refractive index 

1.4640 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Dichloromethane, DMSO, Ethyl Acetate, Methanol

pka

4.01±0.20(Predicted)

form 

Solid

color 

White

optical activity

[α]/D -120.0±2.0°, c = 1 in methanol

InChI

InChI=1S/C9H15NO4/c1-9(2,3)14-8(13)10-5-4-6(10)7(11)12/h6H,4-5H2,1-3H3,(H,11,12)/t6-/m0/s1

InChIKey

JWJVSDZKYYXDDN-LURJTMIESA-N

SMILES

N1(C(OC(C)(C)C)=O)CC[C@H]1C(O)=O

CAS DataBase Reference

51077-14-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:ACROS

1-Boc-L-azetidine-2-carboxylic acid Usage And Synthesis

Chemical Properties

white powder

Uses

Protected Azetidine derivative.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

The general procedure for the synthesis of 1-Boc-L-acridine-2-carboxylic acid from di-tert-butyl dicarbonate and (S)-2-carboxycyclobutanamine was as follows:Example 15: (S)-1-(tert-butoxycarbonyl)azetidine-2-carboxylic acid (13). NaOH (420 mg, 10.5 mmol) was slowly added to a mixed solution of ethanol (20 mL) and water (10 mL) of (S)-2-azetidinecarboxylic acid 12 (1.0 g, 10.0 mmol) and di-tert-butyl dicarbonate (2.83 g, 12.5 mmol) at 0 °C. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the ethanol was removed by evaporation and diluted by adding water (20 mL), followed by adjusting the pH with dilute HCl to 3. Extraction was carried out with ethyl acetate (50 mL x 3) and the organic phases were combined. The organic phase was washed sequentially with water (30 mL) and saturated NaCl solution (30 mL) and then dried with Na2SO4. Evaporation to remove the ethyl acetate gave 1.98 g (100% yield) of target product 13 as a white solid.1H NMR (300 MHz, CDCl3) δ 4.79 (m, 1H), 3.93 (m, 2H), 2.46 (m, 2H), 1.48 (s, 9H).

References

[1] Journal of Medicinal Chemistry, 2005, vol. 48, # 24, p. 7637 - 7647
[2] Patent: US2009/68105, 2009, A1. Location in patent: Page/Page column 11
[3] Chemical Communications, 2016, vol. 52, # 7, p. 1354 - 1357
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 1998, vol. 41, # 5, p. 451 - 463
[5] Journal of Medicinal Chemistry, 1999, vol. 42, # 12, p. 2251 - 2259

1-Boc-L-azetidine-2-carboxylic acid(51077-14-6)Related Product Information

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