N-BOC-1,3-DIAMINO-2-PROPANOL Chemical Properties

Melting point:

77-79 °C

Boiling point:

350.2±32.0 °C(Predicted)

Density 

1.090±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

12.22±0.46(Predicted)

Appearance

Off-white to light yellow Solid

optical activity

Consistent with structure

InChI

InChI=1S/C8H18N2O3/c1-8(2,3)13-7(12)10-5-6(11)4-9/h6,11H,4-5,9H2,1-3H3,(H,10,12)

InChIKey

LZNOKWJGNPKUSE-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCC(O)CN

N-BOC-1,3-DIAMINO-2-PROPANOL Usage And Synthesis

Synthesis

The general procedure for the synthesis of tert-butyl (3-amino-2-hydroxypropyl)carbamate from di-tert-butyl dicarbonate and 1,3-diamino-2-propanol was as follows: 0.9 g of 1,3-diamino-2-propanol was added to a reactor equipped with magnetic stirring, and dissolved with 5 mL of 1 M sodium hydroxide solution. Subsequently, 1.0 g of di-tert-butyl dicarbonate was dissolved in 5 mL of 1,4-dioxane and this solution was slowly added dropwise to the reactor. The reaction mixture was stirred at room temperature for 5 hours and then warmed up to 50-65 °C for decompression distillation to remove most of the solvent, and the remaining solvent was dried by a vacuum pump to give a white viscous solid. The crude product was purified by silica gel column chromatography with gradient elution using dichloromethane-methanol-triethylamine (300:30:1, v/v/v) as eluent to give 600 mg of tert-butyl (3-amino-2-hydroxypropyl)carbamate in 69% yield.

References

[1] Patent: CN106893342, 2017, A. Location in patent: Paragraph 0016; 0017
[2] Patent: CN105503920, 2016, A. Location in patent: Paragraph 0011; 0057; 0058
[3] Journal of Medicinal Chemistry, 1998, vol. 41, # 2, p. 236 - 246
[4] Organic and Biomolecular Chemistry, 2014, vol. 12, # 46, p. 9389 - 9404
[5] Patent: WO2005/66172, 2005, A1. Location in patent: Page/Page column 62

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