(R)-N-BOC-3-AMINOBUTYRIC ACID

(R)-N-BOC-3-AMINOBUTYRIC ACID Property

Melting point:

104-107 °C

Boiling point:

339.5±25.0 °C(Predicted)

Density 

1.101±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

pka

4.43±0.10(Predicted)

Appearance

White to off-white Solid

optical activity

Consistent with structure

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-/m1/s1

InChIKey

PYNDHEONPQYIAN-ZCFIWIBFSA-N

SMILES

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

CAS DataBase Reference

159991-23-8(CAS DataBase Reference)

Safety

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H226Flammable liquid and vapour

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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

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

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

(R)-N-BOC-3-AMINOBUTYRIC ACID Chemical Properties,Usage,Production

Chemical Properties

Off-white powder

Uses

(R)-3-(tert-Butoxycarbonylamino)butanoic Acid is a non-proteinogenic amino acid that can be used to synthesize peptide analogs.

Synthesis

General steps: 1. suspend (R)-3-aminobutyric acid (2.415 g, 23.42 mmol) in a solvent mixture of dioxane (15 mL) and water (15.00 mL) at room temperature with stirring. 2. Triethylamine (TEA, 4.90 mL, 35.1 mmol) was added dropwise to the suspension to give a light brown solution. 3. The reaction mixture was cooled to 0 °C and di-tert-butyl dicarbonate (4.69 g, 26.9 mmol) was added in one portion. 4. The reaction mixture was stirred at room temperature for 16 hours. 5. 5. Upon completion of the reaction, the mixture was partitioned between water (80 mL) and ethyl acetate (EtOAc, 80 mL). 6. The aqueous layer was separated and washed with EtOAc. 7. The aqueous layer was acidified to pH=3 with 1 M aqueous KHSO4 and extracted with EtOAc (2 x 80 mL). 8. The EtOAc extracts were combined, washed with saturated aqueous NaCl (2 x 80 mL), dried over anhydrous Na2SO4, filtered and concentrated. 9. (R)-3-((tert-butoxycarbonyl)amino)butyric acid (4.301 g, 21.16 mmol, 90% yield) was obtained as a pale yellow solid. 10. The product was characterized by XH NMR (400 MHz, CDCl3): δ 4.92 (s, 1H), 4.14-3.96 (m, 2H), 2.56 (d, J=5.2 Hz, 2H), 1.45 (s, 9H), 1.25 (d, J=6.9 Hz, 3H).

References

[1] Patent: WO2012/125622, 2012, A1. Location in patent: Page/Page column 135-136
[2] Chinese Chemical Letters, 2015, vol. 26, # 1, p. 103 - 107
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 5, p. 1421 - 1425
[4] Angewandte Chemie - International Edition, 2018, vol. 57, # 31, p. 9707 - 9710
[5] Angew. Chem., 2018, vol. 130, # 31, p. 9855 - 9858,4