N-Benzyloxycarbonyl-L-proline, CAS No. 1148-11-4

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1148-11-4

Catalog No. EBD2156835

CAS 1148-11-4

Name N-Benzyloxycarbonyl-L-proline

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Basic Information

Synonyms: N-Benzyloxycarbonyl-L-proline Z-L-Proline Z-Pro-OH N-CBZ-L-ProlineN-Carbobenzyloxy-L-proline N-Cbz-L-proline N-Cbz-L-Pro-OH 1-[(benzyloxy)carbonyl]-L-proline 1-[(benzyloxy)carbonyl]-D-proline 1-[(benzyloxy)carbonyl]proline (2S)-1-[(benzyloxy)carbonyl]pyrrolidine-2-carboxylate Cbz-L-proline 1,2-pyrrolidinedicarboxylicacid,1-(phenylmethyl)ester,(2s)- (2s)-1-[(benzyloxy)carbonyl]pyrrolidine-2-carboxylicacid cbz-pro-oh l-cbz-proline benzyloxycarbonyl-l-proline carbobenzyloxy-l-proline N-Carbobenzyloxy-L-proline N-cbz-L-prolinecrystalline

Molecular Formula: C13H15NO4

Molecular Weight: 249.26

MDL Number: MFCD00003170

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates Synthetic Chemistry > Organic Building Blocks > Amines

Product Description:

Cbz-L-Proline is a protected derivative of the naturally occurring amino acid L-proline. It features a carboxybenzyl (Cbz) protecting group on the nitrogen atom of the proline ring, making it a versatile chiral building block in organic synthesis, particularly in peptide chemistry. Its primary application is as a key intermediate in the pharmaceutical industry for the synthesis of various peptide-based drugs and bioactive compounds. The Cbz group serves as a temporary protecting group for the secondary amine, which can be selectively removed under mild hydrogenation conditions without affecting other sensitive functional groups. This compound is crucial for introducing the conformationally constrained proline residue into peptide chains, which can influence the biological activity and stability of the final product. Beyond peptide synthesis, Cbz-L-proline is also employed in the preparation of other proline derivatives and as a chiral auxiliary or ligand in asymmetric synthesis. It is a standard reagent readily available from chemical suppliers for research and development purposes.

Physical Properties

Melting Point: 75-77 °C

Boiling Point: 432.3 °C at 760 mmHg

Flash Point: 215.3 °C

Density: 1.309 g/cm3

Refractivity: -40 ° (C=2, EtOH)

Storage: 2-8°C

Analytical Data

Appearance: white to light yellow crystal powder