1-(tert-Butoxycarbonyl)-4-methylene-L-proline, CAS No. 84348-38-9

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84348-38-9

Catalog No. EBD134428

CAS 84348-38-9

Name 1-(tert-Butoxycarbonyl)-4-methylene-L-proline

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Basic Information

Synonyms: 1-(tert-Butoxycarbonyl)-4-methylene-L-proline N-Boc-4-methylene-L-proline (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLICACID1-TERT-BUTYLESTER 1,2-pyrrolidinedicarboxylicacid,4-methylene-,1-(1,1-dimethylethyl)ester,(2S)- 1-(tert-butoxycarbonyl)-4-methylidene-L-proline 1-Boc-(S)-4-Methylenepyrrolidine-2-carboxylicacid n-t-boc-4-methylene-l-proline boc-4-methylene-l-proline (s)-1-(tert-butoxycarbonyl)-4-methylenepyrrolidine-2-carboxylicacid n-tert-butoxycarbonyl-4-methylene-l-proline

Molecular Formula: C11H17NO4

Molecular Weight: 227.26

MDL Number: MFCD01861787

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates Medicinal Chemistry > Biochemicals and Life Science Reagents > Amino Acids and Derivatives

Product Description:

N-Boc-4-methylene-L-proline is a protected derivative of the non-proteinogenic amino acid L-proline, featuring a Boc (tert-butoxycarbonyl) protecting group on the nitrogen and a methylene group at the 4-position of the proline ring. This specific substitution introduces a reactive exocyclic double bond, making it a versatile chiral building block. Its primary application is in the field of medicinal chemistry and peptide research. The methylene group serves as a key handle for further chemical modifications, such as ring-opening metathesis polymerization (ROMP) to create novel peptide-based polymers or for the synthesis of conformationally constrained peptidomimetics. It is used as a crucial intermediate in the development of protease inhibitors and other bioactive compounds that target various diseases. As a specialty amino acid derivative, it is valued for introducing unique structural motifs and enhancing the metabolic stability of peptide leads. It is typically handled under inert atmosphere due to the potential reactivity of the double bond and stored at low temperatures.

Physical Properties

Melting Point: 110-115 °C

Boiling Point: 349.859 °C at 760 mmHg

Flash Point: 165.389 °C

Density: 1.18 g/cm3