(S)-N-Boc-3-aminobutyric acid Chemical Properties

Melting point:

99 °C

Boiling point:

339.5±25.0 °C(Predicted)

Density 

1.101±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Powder

pka

4.43±0.10(Predicted)

color 

White to light yellow

optical activity

Consistent with structure

Water Solubility 

Slightly soluble in water.

BRN 

6800577

InChI

InChI=1S/C9H17NO4/c1-6(5-7(11)12)10-8(13)14-9(2,3)4/h6H,5H2,1-4H3,(H,10,13)(H,11,12)/t6-/m0/s1

InChIKey

PYNDHEONPQYIAN-LURJTMIESA-N

SMILES

C(O)(=O)C[C@@H](NC(OC(C)(C)C)=O)C

CAS DataBase Reference

158851-30-0(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich

(S)-N-Boc-3-aminobutyric acid Usage And Synthesis

Chemical Properties

White to off-white powder

Uses

(S)-3-(Boc-amino)butyric acid is used for the syntheses of aza-analogues of macrosphelides, synthesis of hybrid peptides with 12/10-helix, and in the synthesis of potentially pharmaceutically active products for the treatment of auto-immune and inflammatory diseases.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

Under argon protection, sodium dihydrogen phosphate (7.0 g) and 34.5% aqueous hydrogen peroxide solution (20 mL) were sequentially added to a solution of tert-butyl (S)-(4-oxobutan-2-yl)carbamate (7.3 g, 39.0 mmol) in acetonitrile (50 mL), and the reaction mixture was stirred at 0 °C for 10 min. Subsequently, a solution of sodium chlorite (6.0 g) in water (20 mL) was added dropwise to the reaction system and stirring was continued at 0 °C for 1 hour. Upon completion of the reaction, the reaction was quenched with saturated sodium bicarbonate solution and the aqueous phase was washed with dichloromethane. The aqueous layer was acidified with 10% hydrochloric acid and extracted with dichloromethane, the organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was identified by 1H-NMR as carboxylic acid (8) (6.0 g, 29.6 mmol, 76% yield), which could be used in the next reaction without further purification.

References

[1] Tetrahedron, 2011, vol. 67, # 40, p. 7681 - 7685

(S)-N-Boc-3-aminobutyric acid(158851-30-0)Related Product Information

• tert-Butanol
• Phenprobamate
• tert-Butyl peroxyacetate
• 4-Aminobutyric acid
• EC 2.6.1.2
• D-Alanine
• Stearic acid
• Butyric Acid
• Ethyl 2-(Chlorosulfonyl)acetate
• DL-2-Aminobutyric acid
• DL-3-Aminobutyric acid
• L(+)-2-Aminobutyric acid
• Folic acid
• Citric acid
• Ascoric Acid
• r-Amino Butryric Acid
• Boc-D-aspartic acid 4-benzyl ester
• Boc-D-aspartic acid 4-cyslohexyl ester