BOC-DL-3-AMINOBUTYRIC ACID

BOC-DL-3-AMINOBUTYRIC ACID Property

Melting point:

98-100 °C

Boiling point:

339.5±25.0 °C(Predicted)

Density 

1.101±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

4.43±0.10(Predicted)

Appearance

White to off-white Solid

Safety

HazardClass 

IRRITANT

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

BOC-DL-3-AMINOBUTYRIC ACID Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 3-[[(1,1-dimethylethoxy)carbonyl]amino]butanoic acid from DL-3-aminobutyric acid (CAS No. [541-48-02], 18.72 g, 176.09 mmol) and di-tert-butyl dicarbonate (39.62 g, 176.09 mmol) is as follows: first, DL-3-aminobutyric acid was dissolved in 96 mL of water, followed by the addition of a 76 mL aqueous solution of di-tert-butyl dicarbonate and NaOH (8.03 g, 200.74 mmol), followed by the addition of tert-butanol (132 mL). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the reaction solution was concentrated under vacuum, then diluted with 200 mL of ethyl acetate and acidified by adjusting to pH 3 with dilute hydrochloric acid. After standing and layering, the aqueous phase was extracted with 200 mL of ethyl acetate. The organic phases were combined, dried with magnesium sulfate, filtered and concentrated in vacuum to give 34.5 g of the target compound as a colorless oil in 82% yield. NMR hydrogen spectrum (300MHz, CDCl3, δ, ppm): 1.25 (d, J = 7.0Hz, 3H); 1.45 (s, 9H); 2.55 (m, 2H); 4.04 (m, 1H); 4.93 (broad peak, 1H); 8.41 (broad peak, 1H).

References

[1] Journal of Organic Chemistry, 2001, vol. 66, # 20, p. 6541 - 6544
[2] Organic Letters, 2012, vol. 14, # 1, p. 398 - 401
[3] Patent: WO2017/76998, 2017, A1. Location in patent: Page/Page column 161
[4] Organic Letters, 2005, vol. 7, # 21, p. 4781 - 4784
[5] Synlett, 2004, # 15, p. 2709 - 2712