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CAS 5211-23-4

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N-carbobenzyloxy-L-proline methyl ester

Description:
N-carbobenzyloxy-L-proline methyl ester, with the CAS number 5211-23-4, is a chemical compound that belongs to the class of amino acid derivatives. It features a proline backbone, which is an important amino acid in protein synthesis, modified by a carbobenzyloxy (Cbz) protecting group and a methyl ester functional group. This compound is typically a white to off-white solid and is soluble in organic solvents such as methanol and dichloromethane, but has limited solubility in water. The Cbz group serves as a protective moiety, making it useful in peptide synthesis by preventing unwanted reactions at the amino group. The methyl ester enhances the compound's lipophilicity, facilitating its incorporation into various chemical reactions. N-carbobenzyloxy-L-proline methyl ester is often utilized in organic synthesis, particularly in the preparation of peptides and other bioactive molecules, due to its ability to undergo selective reactions while maintaining the integrity of the proline structure. Its stability and reactivity make it a valuable intermediate in medicinal chemistry and pharmaceutical research.
Formula:C14H17NO4
InChI:InChI=1/C14H17NO4/c1-18-13(16)12-8-5-9-15(12)14(17)19-10-11-6-3-2-4-7-11/h2-4,6-7,12H,5,8-10H2,1H3/t12-/m0/s1
SMILES:COC(=O)[C@@H]1CCCN1C(=O)OCc1ccccc1
Synonyms:
  • 1-benzyl 2-methyl (2S)-pyrrolidine-1,2-dicarboxylate
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