Boc-L-alanine N-methoxy-N-methyl amide
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Boc-L-alanine N-methoxy-N-methyl amide

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An α-Amino Weinreb amide. Reduced by LiAlH4 to give the corresponding Boc-amino acid aldehyde.

Category
BOC-Amino Acids
Catalog number
BAT-000400
CAS number
87694-49-3
Molecular Formula
C10H20N2O4
Molecular Weight
232.3
Boc-L-alanine N-methoxy-N-methyl amide
IUPAC Name
tert-butyl N-[(2S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]carbamate
Synonyms
Boc-L-Ala-N(OCH3)CH3; Boc-Ala-NMe(OMe); (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate
Appearance
White solid
Purity
≥ 98 % (HPLC)
Density
1.07 g/cm3
Melting Point
148-153 °C (lit.)
Storage
Store at 2-8 °C
InChI
InChI=1S/C10H20N2O4/c1-7(8(13)12(5)15-6)11-9(14)16-10(2,3)4/h7H,1-6H3,(H,11,14)/t7-/m0/s1
InChI Key
PWQIGBOSLQHOBT-ZETCQYMHSA-N
Canonical SMILES
CC(C(=O)N(C)OC)NC(=O)OC(C)(C)C

Boc-L-alanine N-methoxy-N-methyl amide, a chemical compound with diverse applications in peptide synthesis and organic chemistry, plays a crucial role in several key areas with high perplexity and burstiness:

Peptide Synthesis: At the forefront of peptide synthesis, Boc-L-alanine N-methoxy-N-methyl amide serves as a fundamental building block in the solid-phase assembly of peptides. The presence of its Boc (tert-butyloxycarbonyl) protecting group ensures the selective protection of the amino group during coupling reactions enabling the meticulous stepwise construction of peptide chains with unparalleled precision and efficiency.

Drug Design: In the realm of medicinal chemistry, Boc-L-alanine N-methoxy-N-methyl amide emerges as a pivotal precursor for crafting peptide-based drugs. Its integration into peptide sequences bolsters the stability and bioavailability of therapeutic peptides. Furthermore, the compound's shielded amine and carboxyl groups facilitate a myriad of chemical modifications fostering the development of innovative drug candidates with enhanced properties.

Proteomics: Within the domain of proteomics research, Boc-L-alanine N-methoxy-N-methyl amide assumes a critical role as a reagent for modifying and labeling proteins. This modification aids in unveiling intricate protein-protein interactions and post-translational modifications enriching our understanding of cellular processes. The compound's ability to introduce specific functional groups into peptides proves invaluable for advanced analytical techniques like mass spectrometry.

Organic Synthesis: A versatile intermediate in organic synthesis, Boc-L-alanine N-methoxy-N-methyl amide empowers chemists in crafting complex organic molecules. With its robust Boc protecting group allowing for selective deprotection and subsequent functionalization at various stages of the synthetic pathway, this compound emerges as a pivotal tool in the creation of diverse organic entities ranging from natural products to pharmaceuticals.

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