Propanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy- (9CI)

Propanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy- (9CI) Property

Boiling point:

391.7±32.0 °C(Predicted)

Density 

1.240±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

3.58±0.11(Predicted)

Appearance

White to off-white Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Propanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy- (9CI) Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of N-Boc-3-amino-2-hydroxypropionic acid from DL-isoserine (1 g, 9.52 mmol) and di-tert-butyl dicarbonate (2.7 g, 12.37 mmol) was as follows: DL-isoserine (1 g, 9.52 mmol) was dissolved in a solvent mixture of tert-butanol (40 mL) and 1 M aqueous NaOH (20 mL). Di-tert-butyl dicarbonate (2.7 g, 12.37 mmol) was added slowly under cooling in an ice bath. The reaction mixture was stirred at room temperature overnight. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the complete consumption of the raw material, the solvent was removed by concentration under reduced pressure in a water bath at 40 °C. Subsequently, three liquid-liquid extractions were performed with ethyl acetate and 1 M HCl, and the organic phases were combined and washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and concentrated again under reduced pressure in a water bath at 40 °C to afford N-Boc-3-amino-2-hydroxypropionic acid (1.95 g, 100% yield). The product was characterized by 1H-NMR (500 MHz, CDCl3) with the following chemical shifts: δ 1.45 (9H, s), 3.51-3.65 (2H, m), 4.32 (1H, m), 5.10 (1H, br).

References

[1] Patent: US2016/151506, 2016, A1. Location in patent: Paragraph 0284-0288
[2] Chemical and pharmaceutical bulletin, 2002, vol. 50, # 2, p. 239 - 252
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 22, p. 9447 - 9462
[4] Patent: WO2004/39814, 2004, A1. Location in patent: Page 111 - 112
[5] Patent: WO2011/146354, 2011, A1. Location in patent: Page/Page column 61