N-TERT-BUTOXYCARBONYL-DL-TRYPTOPHAN

N-TERT-BUTOXYCARBONYL-DL-TRYPTOPHAN Property

Melting point:

131 °C(dec.)

Boiling point:

535.7±45.0 °C(Predicted)

Density 

1.262±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

powder to crystal

pka

4.00±0.10(Predicted)

color 

White to Light yellow

optical activity

-0.5°(C=0.01 g/ml DMF)

Safety

HS Code 

2933.99.8290

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

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

N-TERT-BUTOXYCARBONYL-DL-TRYPTOPHAN Chemical Properties,Usage,Production

Synthesis

Step 3. General procedure for the preparation of BOC-D-tryptophan. To a solution of water (54 mL) containing NaOH (2.2 g, 55.0 mmol) was added DL-tryptophan (10.0 g, 49.0 mmol) and 1,4-dioxane (36 mL). Subsequently, di-tert-butyl dicarbonate (Boc2O, 10.7 g, 49.1 mmol) was added slowly and dropwise to the above mixture. The reaction mixture was stirred at room temperature for 24 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and the completion of the reaction was indicated by the unfolding of dichloromethane: methanol = 10:1 and an Rf value of 0.5. The reaction mixture was adjusted to pH 6.0 with solid citric acid and subsequently extracted with ethyl acetate (EtOAc, 30 mL x 3). The organic layers were combined, dried and concentrated to give a colorless oil. The residue was washed with petroleum ether (100 mL) and filtered, and the filter cake was further washed with petroleum ether and dried to give BOC-D-tryptophan (14.8 g, 99.0% yield) as a final white solid.

References

[1] Patent: WO2014/14937, 2014, A1. Location in patent: Paragraph 0125; 0128
[2] Patent: CN104876930, 2017, B. Location in patent: Paragraph 0054-0056
[3] Patent: US2010/297756, 2010, A1
[4] Chemistry - A European Journal, 2015, vol. 21, # 51, p. 18589 - 18593
[5] European Journal of Medicinal Chemistry, 2018, vol. 145, p. 140 - 153