L-proline tert-butyl ester hydrochloride, CAS No. 5497-76-7

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5497-76-7

Catalog No. EBD7160

CAS 5497-76-7

Name L-proline tert-butyl ester hydrochloride

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Basic Information

Synonyms: t-butyl-L-prolinatehydrochloride L-prolinetert-butylesterhydrochloride L-PROLINET-BUTYLESTERHYDROCHLORIDESALT L-PROLINE,1,1-DIMETHYLETHYLESTER,HYDROCHLORIDE H-PRO-OBUTHCL H-PRO-OTBUHCL H-PRO-OTBUHYDROCHLORIDE tert-butyl(2s)-pyrrolidine-2-carboxylatehydrochloride L-PROLINET-BUTYLESTERHYDROCHLORIDE Proootbu.hcl tert-butylL-prolinatehydrochloride L-ProlineT-butylesterHCl L-Prolinetert.butylesterhydrochloride H-Pro-OtBu·HCl L-PROLINET-BUTYL

Molecular Formula: C9H18ClNO2

Molecular Weight: 207.7

MDL Number: MFCD00153459

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

Product Description:

L-Proline tert-butyl ester hydrochloride is a white to off-white crystalline powder derived from the amino acid L-proline. It is a protected form of proline where the carboxylic acid group is esterified with a tert-butyl group, and the amine group is present as its hydrochloride salt. This protection strategy enhances its solubility in organic solvents and makes it a versatile intermediate in peptide synthesis and medicinal chemistry. This compound is primarily used as a key chiral building block in the synthesis of various pharmaceuticals and bioactive peptides. Its rigid pyrrolidine ring structure is a crucial scaffold found in many drug molecules, contributing to conformational restriction and influencing biological activity. It serves as a critical intermediate in the production of angiotensin-converting enzyme (ACE) inhibitors, antiviral agents, and other therapeutic compounds. As a protected amino acid derivative, it is a staple reagent in solid-phase peptide synthesis (SPPS) and solution-phase peptide coupling reactions. The tert-butyl ester protecting group is stable under typical peptide coupling conditions and can be selectively removed under mild acidic conditions, such as with trifluoroacetic acid (TFA), without affecting other sensitive functional groups.

Physical Properties

Melting Point: 110-112°C

Boiling Point: 219.2 ºC at 760 mmHg

Flash Point: 86.4 ºC

Storage: 0-6°C

Analytical Data

Appearance: white - off-white powder