BOC-L-NORLEUCINE

BOC-L-NORLEUCINE Property

Boiling point:

373.37°C (rough estimate)

Density 

1.1202 (rough estimate)

refractive index 

1.4425

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

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

form 

Powder

pka

4.02±0.21(Predicted)

color 

Colorless to light yellow

optical activity

[α]20/D 8±1°, c = 1% in methanol

BRN 

3608376

CAS DataBase Reference

6404-28-0(CAS DataBase Reference)

Safety

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29224985

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

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

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.

P501Dispose of contents/container to..…

BOC-L-NORLEUCINE Chemical Properties,Usage,Production

Uses

A boc protected amino acid derivative

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

The general procedure for the synthesis of N-BOC-L-norleucine from L-norleucine and di-tert-butyl dicarbonate was as follows: free L-norleucine (400 mg, 3.05 mmol) was dissolved in a solvent mixture of water and THF (8.8 mL:8.8 mL), NaHCO3 (768 mg, 9.15 mmol) was added and di-tert-butyl dicarbonate ( 800 mg, 3.66 mmol). The reaction mixture was stirred at 0 °C for 30 min, then gradually warmed to room temperature and continued to stir overnight. Upon completion of the reaction, water (10 mL) was added to dissolve any precipitate that may have formed. Unreacted di-tert-butyl dicarbonate was removed by three extractions with petroleum ether. N-BOC-L-norleucine in the aqueous phase was acidified to pH ≈ 3 with 1 M NaHSO4 solution and subsequently extracted three times with EtOAc. The organic layers were combined and dried with Na2SO4. The solvent was removed by concentration under reduced pressure to give the clear oily product N-BOC-L-norleucine (573 mg, 81% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 12.38 (bs, 1H, COOH), 7.02 (d, J=8.2 Hz, 1H, NH), 3.87-3.78 (m, 1H, CH), 1.69-1.47 (m, 2H, CH2), 1.37 (s, 9H, t-Bu), 1.32- 1.20 (m, 4H, CH2), 0.85 (t, J=7.0Hz, 3H, CH3).

References

[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 21, p. 6891 - 6899
[2] Bioorganic and medicinal chemistry letters, 2004, vol. 14, # 1, p. 275 - 278