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IdentificationBack Directory
[Name]

CBZ-L-PHENYLALANINAL
[MDL Number]

MFCD00798796
Chemical PropertiesBack Directory
[Melting point ]

82 °C
[Boiling point ]

450.4±45.0 °C(Predicted)
[pka]

11.17±0.46(Predicted)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[Synthesis]

Carbamic acid, N-?[(1S)?-?2-?(methoxymethylamino)?-?2-?oxo-?1-?(phenylmethyl)?ethyl]?-?, phenylmethyl ester

114744-85-3

CBZ-L-PHENYLALANINAL

59830-60-3

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
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