BOC-GLY-NH2 Chemical Properties

Melting point:

85-87 °C

Boiling point:

339.7±25.0 °C(Predicted)

Density 

1.107±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

form 

Solid

pka

12.01±0.46(Predicted)

color 

White

InChI

InChI=1S/C7H14N2O3/c1-7(2,3)12-6(11)9-4-5(8)10/h4H2,1-3H3,(H2,8,10)(H,9,11)

InChIKey

RHONTQZNLFIDCQ-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCC(N)=O

Safety Information

HS Code 

2924297099

BOC-GLY-NH2 Usage And Synthesis

Uses

Boc-Glycinamide is a useful synthetic intermediate. It is used to prepare primary amides as selective inhibitors of cathepsin K. It is also used to prepare group A streptococcal vaccine.

Synthesis

Boc-Gly-OH (1.00 g, 5.70 mmol) was dissolved in anhydrous THF (16.0 mL) under nitrogen protection and cooled to 0°C. To this solution was added DIPEA (1.2 mL, 6.84 mmol) and stirred at 0 °C for 30 min. Subsequently, 2,2,2-trichloroethyl chloroformate (0.94 mL, 6.84 mmol) was quickly added and stirring was continued for 30 minutes. Then, a mixture of pre-formulated aqueous NH3 solution (2.0 mL) with THF (2.0 mL) was added. The reaction mixture was gradually warmed up to room temperature and stirred continuously for 16 hours. Upon completion of the reaction, the mixture was concentrated under reduced pressure and the resulting residue was extracted by partitioning with EtOAc (40 mL) and water (40 mL). The aqueous layer was further extracted with EtOAc (2 x 30 mL), and all organic layers were combined and washed sequentially with saturated aqueous NaHCO3 solution (30 mL), water (30 mL) and brine (30 mL). The organic layer was dried with MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford the target compound glycinamide (798 mg, 80% yield) as a colorless oil.

References

[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 834 - 864
[2] Tetrahedron, 2018, vol. 74, # 15, p. 1951 - 1956
[3] Tetrahedron Letters, 2005, vol. 46, # 40, p. 6879 - 6882
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 4994 - 4997
[5] Tetrahedron Letters, 2003, vol. 44, # 39, p. 7325 - 7328

BOC-GLY-NH2(35150-09-5)Related Product Information

• tert-butyl N-[(1s,3s)-3-{[imino(methyl)oxo-lambda6-sulfanyl]methyl}cyclobutyl]carbamate, cis
• tert-butyl N-[(1R)-1-cyclohexylethyl]carbamate
• (3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone
• TERT-BUTYL N-(6-HYDROXYHEXYL)CARBAMATE
• tert-butyl N-[(2S)-5-bromo-4-oxopentan-2-yl]carbamate
• tert-butyl N-[(2R,3S)-3-aminobutan-2-yl]carbamate hydrochloride
• (S)-(2-Amino-3,3-dimethyl-butyl)-carbamic acid tert-butyl ester
• tert-butyl N-(azetidin-3-yl)-N-(2-methoxyethyl)carbamate
• tert-butyl N-[(1-methyl-3-oxocyclopentyl)methyl]carbamate
• Carbamic acid, (phenylsulfonyl)-, 1,1-dimethylethyl ester
• N-(tert-Butoxycarbonyl)glycylglycine
• Glycinamide
• BOC-MET-LEU-PHE-OH
• BOC-ALA-ALA-OH
• BOC-PHE-SER-ARG-AMC ACETATE SALT
• BOC-GLY-GLY-LEU-PNA
• BOC-VAL-PRO-ARG-MCA
• BOC-PRO-PRO-OH