L-Alanine tert.butyl ester hydrochloride is a protected amino acid ester derived from L-alanine, featuring an alanine backbone bearing a tert-butyl ester at the carboxyl terminus and a free amino functionality associated with hydrochloride salt formation. The molecule contains the amino group and an esterified carboxyl group, with the tert-butyl ester masking the carboxyl as an acid-labile protecting group while the hydrochloride counterion stabilizes the amino group for handling and downstream coupling chemistry. As an amino acid ester salt, it is used as a substrate in peptide synthesis workflows and in the preparation of alanine-containing peptide intermediates where controlled carboxyl activation and stepwise assembly of amide bonds are required.
CAT No: CP00134
CAS No:13404-22-3
Synonyms/Alias:13404-22-3;L-Alaninetert-butylesterhydrochloride;tert-butyll-alaninatehydrochloride;(S)-tert-Butyl2-aminopropanoatehydrochloride;H-Ala-OtBu.HCl;MFCD00035524;ST51037485;H-Ala-OtBuinvertedexclamationmarkcurrencyHCl;(S)-2-AminopropionicAcidtert-ButylEsterHydrochloride;Ala-OtBu.HCl;H-Ala-OBut??HCl;PubChem10948;H-ALA-OTBUHCL;tert-ButylalaninateHCl;H-Ala-OtBuhydrochloride;Tert-butyl(2S)-2-aminopropanoateHydrochloride;KSC174M8P;A0255_SIGMA;L-alaninetertbutylesterHCl;SCHEMBL214837;t-butylalaninatehydrochloride;05190_FLUKA;CTK0H4687;MolPort-003-925-461;tert-Butylalaninatehydrochloride
L-Alanine tert.butyl ester hydrochloride is an alanine-derived amino acid ester presented as the hydrochloride salt, featuring the L-configured stereocenter at the alpha-carbon and a tert-butyl ester that can be used as a protected carboxyl functionality during synthesis. The molecule contains a primary amino group as a salt-associated functionality, enabling controlled handling and subsequent conversion to peptide-ready forms through base-mediated deprotonation and coupling-compatible activation. The tert-butyl ester provides acid-labile carboxyl protection, supporting selective deprotection strategies that preserve other sensitive functionalities in multi-step sequences. The overall reactivity profile aligns with amino acid ester synthesis, chiral intermediate preparation, and downstream transformation into amide linkages or carboxylic acid derivatives for peptide and fine-chemical construction.
1. Peptide Coupling Chemistry
L-Alanine tert.butyl ester hydrochloride supports peptide building block preparation in synthetic organic chemistry by providing an L-alanine ester form with a protected carboxyl group suitable for activation and coupling. The presence of the alpha-amino functionality as a hydrochloride salt can be managed to enable formation of peptide bonds after conversion to the appropriate nucleophilic amine state. The tert-butyl ester can be retained during coupling steps and then removed under conditions compatible with protecting-group strategies used for other residues. Downstream use includes generating alanine-containing peptide fragments, dipeptide intermediates, and protected alanine derivatives for iterative chain assembly.
2. Protected Amino Acid Intermediate
L-Alanine tert.butyl ester hydrochloride functions as a chiral amino acid intermediate for protected amino acid synthesis where controlled carboxyl protection is required. The tert-butyl ester serves as an acid-labile handle that can be selectively deprotected to yield the corresponding carboxylic acid for subsequent derivatization, including conversion to activated acids or amide-forming reagents. The L-configuration at the alpha-carbon provides stereochemical integrity for stereospecific peptide construction and for maintaining defined stereochemistry in downstream SAR studies. The hydrochloride salt form also assists in handling and storage of the amino functionality during multi-step synthesis, enabling consistent intermediate management.
3. Side-Chain Functionalization Routes
L-Alanine tert.butyl ester hydrochloride can be incorporated into side-chain functionalization workflows where alanine serves as a minimal chiral scaffold for constructing substituted derivatives. The ester-protected carboxyl group allows selective transformation of the amino functionality through temporary protection, acylation, or coupling-ready conversion while keeping the carboxyl group protected. The alpha-amino and ester functionalities can be used to access N-functionalized alanine derivatives, including amide formation with carboxylic acid partners and preparation of alanine-based fragments for combinatorial library synthesis. The resulting carboxylic acid after tert-butyl deprotection can further support downstream formation of salts, esters, or activated intermediates used in fine chemical and peptide analog synthesis.
4. Pharmaceutical Intermediate Preparation
L-Alanine tert.butyl ester hydrochloride is suitable for pharmaceutical intermediate preparation in process chemistry and fine chemical manufacturing contexts where alanine-derived chiral fragments are required. The tert-butyl ester provides a protected carboxyl group that can be carried through synthetic sequences and then converted to the free acid to enable formation of amide linkages, prodrug-like ester motifs, or key coupling intermediates. The hydrochloride salt form can be leveraged for controlled reactivity of the amino group during manufacturing-scale stepwise transformations. Downstream utility includes serving as a feedstock for alanine-containing building blocks used in synthesis of small-molecule intermediates, peptidomimetic fragments, and stereochemically defined chiral precursors.
5. Analytical Standards And Labeling Precursors
L-Alanine tert.butyl ester hydrochloride can be applied in analytical research as a reference material precursor for method development involving amino acid ester chemistry and deprotection behavior. The defined L-stereochemistry and ester form support consistent chromatographic and derivatization patterns when developing workflows for amino acid ester detection, peptide hydrolysate profiling, or carboxyl-protection strategy verification. The compound's functional groups enable conversion into labeled or derivatized analogs used to calibrate analytical instruments and validate sample preparation steps. Downstream formation of the corresponding carboxylic acid or activated derivatives after tert-butyl deprotection can further support preparation of standards for peptide coupling monitoring and impurity characterization in amino acid derivative synthesis.
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