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Methyl 2-((tert-butoxycarbonyl)amino)-2-methylpropanoate

  • CAS No. 84758-55-4

  • Cat. No. CS-0154459
  • Purity≥98%
  • MDL No.MFCD20484740

*For research and further manufacturing use only, not for direct human use.

Methyl 2-((tert-butoxycarbonyl)amino)-2-methylpropanoate|CS-0154459

Structure of 84758-55-4

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General Information

  • CAS No. 84758-55-4
  • Cat. No. CS-0154459
  • Purity ≥98%
  • MDL No. MFCD20484740
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₉NO₄
  • Molecular Weight 217.26
  • Synonym(s) N - (tert - butoxycarbonyl) - ± - Methylalanine Methyl ester
  • SMILES CC(C)(OC(NC(C)(C(OC)=O)C)=O)C

Description

Methyl 2-((tert-butoxycarbonyl)amino)-2-methylpropanoate is a bench-stable, moisture-tolerant amino acid equivalent featuring a sterically hindered α-carbon. This protected serine surrogate integrates seamlessly into peptide synthesis workflows, enabling efficient coupling and selective deprotection under mild acidic conditions. The tert-butyl carbamate group provides robust protection for the amine, while the methyl ester facilitates downstream functionalization.

Application

Methyl 2-((tert-butoxycarbonyl)amino)-2-methylpropanoate serves as a stable, bench-ready building block for the synthesis of sterically hindered amino acid derivatives and peptidomimetics. The tert-butyl carbamate (Boc) group enables orthogonal protection of primary amines, while the methyl ester supports facile hydrolysis or coupling reactions. Its resistance to racemization and compatibility with standard peptide coupling protocols makes it ideal for modular solid-phase and solution-phase syntheses.

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   64.63
  • LogP   1.4627
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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