TERT-BUTYL N-(1-BENZYL-2-HYDRAZINO-2-OXOETHYL)CARBAMATE Chemical Properties

Melting point:

131-136°C

Boiling point:

505.3±50.0 °C(Predicted)

Density 

1.146±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

pka

11.42±0.46(Predicted)

form 

solid

color 

Off white

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

Hazard Note 

Irritant

HS Code 

2922500090

TERT-BUTYL N-(1-BENZYL-2-HYDRAZINO-2-OXOETHYL)CARBAMATE Usage And Synthesis

Synthesis

General procedure for the synthesis of tert-butyl (S)-(1-hydrazino-1-oxo-3-phenylpropan-2-yl)carbamate from N-Boc-L-phenylalanine methyl ester: Hydrazine hydrate (170 μL, 3.44 mmol) was added to a methanol (5.4 mL) solution of N-Boc-L-phenylalanine methyl ester (300 mg, 1.07 mmol). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was concentrated under reduced pressure by rotary evaporator. The resulting residue was first ground with hexane (2×) and then with a minimum volume of 2:3 hexane/methanol solvent mixture (2×) to afford the target product (S)-(1-hydrazino-1-oxo-3-phenylpropan-2-yl)carbamic acid tert-butyl ester in white solid form (195 mg, 65% yield). The structure of the product was confirmed by 1H NMR (CDCl3) δ 7.41-7.25 (m, 3H), 7.20 (d, J = 6.8 Hz, 2H), 4.39-4.21 (m, 1H), 3.07 (d, J = 7.0 Hz, 2H), 1.42 (s, 9H) and mass spectrometry (ESI+) m/z 280.3 ([M+H]+).

References

[1] New Journal of Chemistry, 2018, vol. 42, # 6, p. 4344 - 4351
[2] Journal of Organic Chemistry, 1995, vol. 60, # 10, p. 3112 - 3120
[3] Angewandte Chemie - International Edition, 2016, vol. 55, # 32, p. 9422 - 9426
[4] Angew. Chem., 2016, vol. 55, # 32, p. 9569 - 9574,6
[5] Patent: WO2013/192286, 2013, A1. Location in patent: Paragraph 00281

TERT-BUTYL N-(1-BENZYL-2-HYDRAZINO-2-OXOETHYL)CARBAMATE(30189-48-1)Related Product Information

• N-(tert-Butoxycarbonyl)-L-phenylalanine
• Boc-Glycine hydrazide
• H-PHE-NHNH2
• TERT-BUTYL N-(1-BENZYL-2-HYDRAZINO-2-OXOETHYL)CARBAMATE