BOC-D-4-Chlorophe

BOC-D-4-Chlorophe Property

Melting point:

~110 °C

alpha 

-24 º (c=1,EtOH)

Boiling point:

452.5±40.0 °C(Predicted)

Density 

1.2167 (rough estimate)

refractive index 

1.6800 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

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

form 

Powder

pka

3.83±0.10(Predicted)

color 

White

optical activity

[α]20/D 26±2°, c = 1% in ethyl acetate

BRN 

5381988

CAS DataBase Reference

57292-44-1(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29242990

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-D-4-Chlorophe Chemical Properties,Usage,Production

Chemical Properties

white powder

Uses

N-(tert-Butoxycarbonyl)-D-4-chlorophenylalanine, is one of the phenylalanine derivatives, that can be used for the synthesis of THIQ (C380165), which is a selective melanocortin 4 receptor.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

The general procedure for the synthesis of (R)-2-((tert-butoxycarbonyl)amino)-3-(4-chlorophenyl)propanoic acid from D-4-chlorophenylalanine was as follows: the crude product of D-4-chlorophenylalanine (22.0 mg, 0.110 mmol) was dissolved in a mixed solvent of water (2 mL) and acetone (1.0 mL). To this solution was sequentially added a solution of acetone (0.5 mL) of di-tert-butyl dicarbonate (Boc)2O (40.4 mg, 0.185 mmol) and a solution of acetone (0.5 mL) of triethylamine (18.8 mg, 0.186 mmol). The reaction mixture was stirred at room temperature for 44 hours. Upon completion of the reaction, the mixture was concentrated to a volume of ≤ 2 mL, followed by the addition of toluene (5 mL). The pH of the aqueous layer was adjusted to 2-3 by slowly adding 4N hydrochloric acid under stirring. the organic layer was separated and washed with saturated saline (5 mL x 2). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent to give Boc-D-4-chlorophenylalanine (28.7 mg, 87.3% yield, ee value 98.6%) as a white solid. The product was analyzed by HPLC under the following conditions: column: CHIRALPAK AD-RH (5 μm, 150×4.6 mm ID); mobile phase: A (0.1% aqueous phosphoric acid solution):B (0.1% phosphoric acid acetonitrile solution)=35:65; flow rate: 1.0 mL/min; column temperature: 35°C; detection wavelength: 254 nm. The analytical results showed that the target The retention time of the compound Boc-D-4-chlorophenylalanine was 14.16 min, the isomer ratio was 0.7:99.3, and the corresponding ee value was 98.6%.

References

[1] Patent: US2016/102045, 2016, A1. Location in patent: Paragraph 0300-0307