(R)-N-BOC-Propargylglycine Chemical Properties

Melting point:

86-88°

Boiling point:

353.22°C (rough estimate)

Density 

1.2177 (rough estimate)

refractive index 

1.4368 (estimate)

storage temp. 

2-8°C

pka

3.53±0.10(Predicted)

form 

Crystalline Powder

color 

Off-white to light beige

optical activity

-32.6364°(C=1.1311 g/100ml CHCL3)

InChI

InChI=1S/C10H15NO4/c1-5-6-7(8(12)13)11-9(14)15-10(2,3)4/h1,7H,6H2,2-4H3,(H,11,14)(H,12,13)/t7-/m1/s1

InChIKey

AMKHAJIFPHJYMH-SSDOTTSWSA-N

SMILES

C(O)(=O)[C@H](NC(OC(C)(C)C)=O)CC#C

CAS DataBase Reference

63039-46-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

HS Code 

29224985

MSDS

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(R)-N-BOC-Propargylglycine Usage And Synthesis

Chemical Properties

off-white to light beige crystalline powder

Uses

(R)-2-((tert-Butoxycarbonyl)amino)pent-4-ynoic acid is a Glycine.html" class="link-product" target="_blank">Glycine (HY-Y0966) derivative[1]. (R)-2-((tert-Butoxycarbonyl)amino)pent-4-ynoic acid is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

Synthesis

Step 5: Preparation of (R)-2-((tert-butoxycarbonyl)amino)pent-4-ynoic acid L-alkynylglycine (10 g) [prepared according to Schwyzer et al, Helv. Chim. Acta, 59, 2181 (1976)] was suspended in tetrahydrofuran (30 mL). To this suspension, water (30 mL), potassium carbonate (36.7 g) and di-tert-butyl dicarbonate (21.9 g) were added sequentially. Subsequently, additional water was added to completely dissolve the mixture and the resulting solution was stirred for 12 hours at room temperature. Upon completion of the reaction, the organic solvent was removed by evaporation. The remaining aqueous phase was washed with ether and then acidified with 1N aqueous citric acid to pH 3. The acidified aqueous phase was extracted with dichloromethane, and the organic phases were combined and the solvent was removed by evaporation to afford (R)-2-((tert-butoxycarbonyl)amino)pent-4-ynoic acid (18.9 g, 97% yield), and the product was ready to use in subsequent reactions without further purification.

References

[1] Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144. DOI:10.1080/10408398.2012.708368

(R)-N-BOC-Propargylglycine(63039-46-3)Related Product Information

• L-Propargylglycine
• (R)-METHYL-2-BOC-AMINO-4-PENTENOIC ACID
• METHYL-2-BOC-AMINO-4-PENTENOIC ACID
• DL-PROPARGYLGLYCINE
• (S)-N-BOC-Propargylglycine
• (R)-2-(((benzyloxy)carbonyl)aMino)pent-4-ynoic acid
• L-Propargylglycine HCL
• (R)-2-aminopent-4-ynoic acid
• (R)-N-BOC-Propargylglycine
• 4-Pentyn-1-ol
• D-PROPARGYLGLYCINE
• 4-Fluorocinnamic acid
• 4-PENTYNOIC ACID
• Cyclohexylamine
• DL-PROPARGYL-GLY-OH
• BOC-(R)-ALPHA-PROPYNYL-PROLINE
• Carbamic acid, [(1R)-1-(hydroxymethyl)-2-propynyl]-, 1,1-dimethylethyl ester
• BOC-D-PRA-OH DCHA