CBZ-L-PHENYLALANINAL

CBZ-L-PHENYLALANINAL Property

Melting point:

82 °C

Boiling point:

450.4±45.0 °C(Predicted)

Density 

1.168

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

pka

11.17±0.46(Predicted)

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.

CBZ-L-PHENYLALANINAL Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of N-Cbz-L-phenylalanine aldehyde from the compound (CAS:114744-85-3) was as follows: lithium aluminum hydride (0.95 mL of a 1.0 M THF solution, 0.95 mmol) was added to a solution containing benzyl [(S)-1-(methoxy-methyl-carbamoyl)-2-phenyl-ethyl]-carbamate (0.30 g of a 0.86 mmol) in a solution of THF (10 mL) and the reaction was carried out at room temperature. The resulting mixture was stirred at room temperature for 2 h. The reaction was subsequently terminated by dilution with the addition of ethyl acetate (200 mL) and washed with 1% aqueous hydrochloric acid (200 mL). The organic layer was dried with magnesium sulfate and concentrated under vacuum. The residue was repeatedly diluted with acetonitrile (2 x 200 mL) and concentrated under vacuum to give 0.24 g (yield as agreed) of benzyl ((S)-1-benzyl-2-oxo-ethyl)-carbamate as a colorless oil, which was used directly in the next reaction without further purification. Mass spectrometry analysis (ES+ LC/MS) showed m/e 284 (M+H), retention time (RT) = 4.75 min.

References

[1] Patent: US2008/139556, 2008, A1. Location in patent: Page/Page column 18; 46
[2] Journal of Organic Chemistry, 2016, vol. 81, # 4, p. 1416 - 1424
[3] Tetrahedron Letters, 2000, vol. 41, # 32, p. 6131 - 6135
[4] Tetrahedron, 1996, vol. 52, # 1, p. 305 - 318
[5] Tetrahedron Letters, 1998, vol. 39, # 11, p. 1341 - 1344