BOC-D-ALA-NH2 Chemical Properties

Melting point:

120-121 °C

Boiling point:

343.1±25.0 °C(Predicted)

Density 

1.081±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

11.38±0.46(Predicted)

Appearance

White to yellow Solid

BOC-D-ALA-NH2 Usage And Synthesis

Synthesis

GENERAL STEPS: To a stirred solution of N-tert-butoxycarbonyl-L-alanine (5.0 g, 26.4 mmol) in anhydrous tetrahydrofuran (THF) at -10 °C were sequentially added triethylamine (3 mL, 21.12 mmol) and ethyl chloroformate (2.5 mL, 26.4 mmol). The reaction mixture was stirred continuously at this temperature for 1 hour, followed by the passage of ammonia (NH3) for 1.5 hours. After completion of ammonia pass-through, the reaction mixture was transferred to room temperature conditions and continued stirring overnight. At the end of the reaction, the THF solvent was removed by distillation under reduced pressure. Subsequently, aqueous sodium chloride solution (40 mL) was added to the residue and extracted several times with ethyl acetate (EtOAc, 5 x 40 mL). The organic phases were combined, washed sequentially with 0.5 M hydrochloric acid (2 × 30 mL), dried with anhydrous sodium sulfate (Na2SO4), filtered, and the solvent was removed by vacuum evaporation to finally obtain the target product, N-Boc-D-alaninamide.

References

[1] Tetrahedron, 1999, vol. 55, # 42, p. 12301 - 12308
[2] Tetrahedron Letters, 2007, vol. 48, # 4, p. 603 - 607
[3] Synthetic Communications, 2013, vol. 43, # 7, p. 993 - 1006
[4] Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 7, p. 2647 - 2648
[5] Tetrahedron Asymmetry, 2013, vol. 24, # 24, p. 1572 - 1575

BOC-D-ALA-NH2(78981-25-6)Related Product Information

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• BOC-D-GLU-NH2
• BOC-D-ASP-NH2
• BOC-D-PRO-D-PHE-OH
• BOC-D-PHE-PRO-OH
• BOC-D-MET-GLY-OH
• 1-T-BOC-PIPERIDINE-4-SPIRO-5'-[1',3'-BIS-T-BOC]-HYDANTOIN
• (R)-3-(BOC-AMINO)-2-OXO-1-PYRROLIDINE-ACETIC ACID
• BOC-D-PHE-PRO-OSU
• (R)-3-(BOC-AMINO)-2-OXO-1-AZEPINE-ACETIC ACID
• BOC-DARG-GLY-ARG-CHO
• N-T-BOC-D-PHE-ALA-NLE P-NITROANILIDE
• BOC-ALA-D-GLU(OBZL)-NH2
• BOC-D-LEU-GLY-GLY-OH
• N-ALPHA-T-BOC-D-VAL-L-LEU-NE-CBZ-L-LYS