Boc-4-amino-1-methylpyrrole-2-carboxylic acid is a Boc-protected, non-proteinogenic amino acid derivative featuring a substituted pyrrole ring with a carboxylic acid at the 2-position and an amino substituent at the 4-position, along with a N-methyl substituent on the heterocycle. The molecule contains a free carboxylic acid functional group and a Boc-protected amino group, where the tert-butoxycarbonyl (Boc) protecting group masks the exocyclic amine to control chemoselectivity and suppress undesired side reactions during stepwise coupling. It is commonly used as a protected building block for peptide and peptidomimetic synthesis where heteroaromatic side-chain functionality and the protected amine enable incorporation into larger amide frameworks under controlled conditions.
CAT No: CP27467
CAS No:77716-11-1
Synonyms/Alias:4-(Boc-amino)-1-methyl-1H-pyrrole-2-carboxylic acid;77716-11-1;4-((tert-Butoxycarbonyl)amino)-1-methyl-1H-pyrrole-2-carboxylicacid;boc-py-oh;4-[(tert-butoxycarbonyl)amino]-1-methyl-1h-pyrrole-2-carboxylicacid;4-(Boc-amino)-1-methylpyrrole-2-carboxylicacid;4-tert-Butoxycarbonylamino-1-methyl-1H-pyrrole-2-carboxylicacid;4-[(tert-butoxycarbonyl)amino]-1-methylpyrrole-2-carboxylicacid;SBB053096;4-amino-1-methyl-1h-pyrrole-2-carboxylicacid,4-bocprotected;4-(boc-amino)-1-methyl-1h-pyrrole-2-carboxylicacid;4-[(tert-Butoxycarbonyl)amino]-2-carboxy-1-methyl-1H-pyrrole;4-[(tert-butoxy)carbonylamino]-1-methylpyrrole-2-carboxylicacid;4-tert-butoxycarbonylamino-1-methyl-1H-pyrrole-2carboxylicacid;4-(tert-butoxycarbonylamino)-1-methyl-1H-pyrrole-2-carboxylicacid;4-[(4-tert-butoxycarbonylamino-1-methyl-1H-pyrrole-2-carboxylicacid;Maybridge1_008798;AC1MC3RJ;ACMC-1BHZ9;Oprea1_532277;boc-nh(4)-mepyl-(2)-oh;17852_ALDRICH;SCHEMBL1845748;17852_FLUKA;CTK2H6944;HMS566H20
Boc-4-amino-1-methylpyrrole-2-carboxylic acid is a Boc-protected amino acid building block featuring a substituted pyrrole ring, providing a rigid heteroaromatic side chain with an N-methyl substituent. The molecule contains a protected α-amino functionality (Boc) and a carboxylic acid suitable for conversion into peptide-coupling intermediates, making it a practical heteroaryl amino acid precursor for constructing modified peptide motifs and peptidomimetic scaffolds.
1. Peptidomimetic Building Block
Boc-4-amino-1-methylpyrrole-2-carboxylic acid is used by medicinal chemistry and chemical biology teams to introduce a heteroaromatic pyrrole motif into peptide-like structures, where the ring electronics and constrained geometry can help tune physicochemical properties and binding-site interactions in structure-activity relationship studies. The Boc-protected amino group supports downstream assembly into amide-linked frameworks, while the pyrrole carboxylic acid functionality enables incorporation as a defined residue within custom peptide analogs and peptidomimetics.
2. Pharmaceutical Intermediate Synthesis
Boc-4-amino-1-methylpyrrole-2-carboxylic acid is commonly positioned as a heteroaryl amino acid intermediate for the preparation of higher-complexity medicinal chemistry targets, including substituted amide derivatives and heteroaryl-containing fragments used in lead optimization. Development chemists select this scaffold because it provides a protected amine and a carboxylic acid handle in the same intermediate, allowing controlled functionalization during route design for heteroaromatic series.
3. Amide Coupling Substrate
Boc-4-amino-1-methylpyrrole-2-carboxylic acid serves as a defined coupling substrate for generating amide-linked products in laboratory synthesis workflows, particularly when a pyrrole-based amino acid motif must be appended to an existing scaffold. Researchers value the presence of the Boc-protected amine for managing reactivity during multi-step synthesis, while the carboxylic acid provides a consistent entry point for standard peptide-coupling strategies used to build heteroaryl-containing derivatives.
4. Heteroaryl Scaffold Diversification
Boc-4-amino-1-methylpyrrole-2-carboxylic acid supports scaffold diversification efforts where the pyrrole ring is leveraged as a stable heteroaromatic core for generating analog libraries. Synthetic teams use this building block to create series of structurally related compounds that differ at the amide linkage or downstream functionalization sites, enabling systematic exploration of how heteroaryl incorporation affects overall molecular properties in preclinical discovery chemistry.
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