Boc-L-2,4-diaminobutyric acid Chemical Properties

Melting point:

192-194 °C

Boiling point:

385.5±37.0 °C(Predicted)

Density 

1.160±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Methanol (Sparingly), Water (Slightly)

form 

Powder

pka

3?+-.0.10(Predicted)

color 

White to off-white

optical activity

[α]/D +7.5±1°, c = 1 in methanol: water (1:1)

BRN 

4745487

CAS DataBase Reference

25691-37-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

38-41

Safety Statements 

26-39

RIDADR 

3265

WGK Germany 

3

HS Code 

2922.49.8000

HazardClass 

8

PackingGroup 

Ⅲ

Boc-L-2,4-diaminobutyric acid Usage And Synthesis

Uses

Boc-L-2,4-diaminobutyric acid is a reagent used to synthesize somatostatin antagonist. It can also be used to develop blood coagulation factor Xa inhibitors.

Synthesis

General procedure for the synthesis of (S)-4-amino-2-((tert-butoxycarbonyl)amino)butanoic acid from BOC-L-glutamine: to a mixed solution of (S)-5-amino-2-(tert-butoxycarbonylamino)-5-oxopentanoic acid (2 g, 8.1 mmol) in DMF and water (1:1, v/v, 18 ml) was added pyridine (1.3 ml, 16.2 mmol). The reaction mixture was stirred at room temperature for 5-10 min. Subsequently, iodobenzene diacetate (3.92 g, 12.1 mmol) was added and the reaction was continued with stirring for 4 hours. After completion of the reaction, deionized water (100 ml) was added to the reaction mixture and extracted with ethyl acetate (3 x 100 ml). The organic phases were combined and washed sequentially with deionized water (100 ml) and saturated saline (100 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by ether milling and after evaporation of the product grades, 1.1 g (62% yield) of the target compound was obtained as a brown solid. LC-MS analysis showed m/z = 219.1 (M + H).

References

[1] Synthetic Communications, 2004, vol. 34, # 6, p. 1049 - 1056
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 15, p. 4650 - 4656
[3] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 1, p. 161 - 175
[4] Patent: WO2014/151472, 2014, A1. Location in patent: Paragraph 00340-00341
[5] Patent: WO2016/40315, 2016, A1. Location in patent: Paragraph 00383; 00384

Boc-L-2,4-diaminobutyric acid(25691-37-6)Related Product Information

• DL-2-Aminobutyric acid
• DL-3-Aminobutyric acid
• 4-Aminobutyric acid
• tert-Butyl carbazate
• L(+)-2-Aminobutyric acid
• D-2-Aminobutyric acid
• Boc-D-2,4-diaminobutyric acid
• N-tert-Butoxycarbonyl-L-glutamic acid gamma-tert-butyl ester
• BOC-OIC-OH
• Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate
• BOC-ASP-OH
• BOC-L-Asparagine
• Boc-N-beta-Trityl-L-asparagine
• N-Boc-cis-4-Fmoc-Amino-L-proline
• FMOC-DAB(BOC)-OH
• Z-DBU(BOC)-OH
• N-GAMMA-BOC-L-2,4-DIAMINOBUTYRIC ACID METHYL ESTER HYDROCHLORIDE
• r-Amino Butryric Acid