(S)-N-BOC-Propargylglycine Chemical Properties

Melting point:

85.5 °C

Boiling point:

353.22°C (rough estimate)

Density 

1.2177 (rough estimate)

refractive index 

1.4368 (estimate)

storage temp. 

-20°C

pka

3.53±0.10(Predicted)

form 

Crystalline Powder

color 

Off-white to light yellow

optical activity

[α]/D 26.0±2.0°, c = 1 in methanol

Water Solubility 

Soluble in water.

BRN 

5739897

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-/m0/s1

InChIKey

AMKHAJIFPHJYMH-ZETCQYMHSA-N

SMILES

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

CAS DataBase Reference

63039-48-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29241990

MSDS

• Language:English Provider:ACROS

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

Chemical Properties

off-white to light yellow crystalline powder

Uses

N-Boc-2-propargyl-L-glycine is used as pharmaceutical intermediate.

reaction suitability

reaction type: Boc solid-phase peptide synthesis
reaction type: click chemistry

Synthesis

Step 5: Synthesis of Boc-L-ynylglycine 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 reaction mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the organic solvent was removed by evaporation. The resulting aqueous solution was first washed with ether and then acidified with aqueous 1N citric acid to pH 3. The acidified solution was extracted with dichloromethane, and the extract was evaporated to remove the solvent to afford Boc-L-alkynylglycine (18.9 g, 97% yield), which was used in subsequent steps without further purification.

References

[1] Chemistry - An Asian Journal, 2010, vol. 5, # 8, p. 1765 - 1769
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7512 - 7515
[3] Patent: US5212185, 1993, A
[4] Patent: US5298505, 1994, A
[5] Patent: US5373017, 1994, A

(S)-N-BOC-Propargylglycine(63039-48-5)Related Product Information

• L-Propargylglycine
• (R)-N-BOC-PROPARGYLGLYCINE,(R)-N-boc-Propargylglycine(e.e.),(R)-N-BOC-PROPARGYLGLYCINE, 95%, 98% EE,(R)-N-BOC-Propargylglycine, 98% ee
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• (S)-N-BOC-Propargylglycine
• BOC-L-PROPARGYLGLYCINE DCHA SALT
• BOC-(S)-ALPHA-PROPYNYL-PROLINE