1-N-Boc-3-Azetidinecarboxylic acid Chemical Properties

Melting point:

100.1-101.9°C

Boiling point:

321.0±35.0 °C(Predicted)

Density 

1.246±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

4.21±0.20(Predicted)

form 

Crystalline Powder

color 

White

BRN 

8832105

InChI

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

InChIKey

NCADHSLPNSTDMJ-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CC(C(O)=O)C1

CAS DataBase Reference

142253-55-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-37-26

WGK Germany 

3

TSCA 

No

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

1-N-Boc-3-Azetidinecarboxylic acid Usage And Synthesis

Chemical Properties

light yellow powder

Uses

peptide synthesis

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

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).

References

[1] Patent: WO2008/4946, 2008, A1. Location in patent: Page/Page column 90-91
[2] Patent: US2008/171732, 2008, A1. Location in patent: Page/Page column 36
[3] Patent: WO2008/85119, 2008, A1. Location in patent: Page/Page column 175-176
[4] Patent: WO2008/108957, 2008, A2. Location in patent: Page/Page column 98
[5] Patent: WO2008/95912, 2008, A2. Location in patent: Page/Page column 77

1-N-Boc-3-Azetidinecarboxylic acid(142253-55-2)Related Product Information

• tert-Butyl acetate
• 1,2,3,4-Butanetetracarboxylic acid
• 3-Azetidinecarboxylic acid
• ISOBUTANE
• tert-Butanol
• Folic acid
• Quinolinic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• 2,5-PYRIDINEDICARBOXYLIC ACID
• tert-Butyl peroxyacetate
• Lithium tri-tert-butoxyaluminum hydride
• Hyaluronic acid
• n-Butane
• Citric acid
• Ascoric Acid
• 3-(Methylamino)propanoic acid, N-BOC protected
• 1-Boc-Azetidine-3-yl-methanol
• Azetidine