Methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-iodopropanoate
[CAS# 170848-34-7]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Alanine derivatives
• Name: Methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-iodopropanoate
• Synonyms: Boc-3-iodo-D-Ala-OMe
• Molecular Formula: C₉H₁₆INO₄
• Molecular Weight: 329.13
• Protein Sequence: X
• CAS Registry Number: 170848-34-7
• EC Number: 890-205-9
• SMILES: CC(C)(C)OC(=O)N[C@H](CI)C(=O)OC

Properties

• Density: 1.6±0.1 g/cm³ Calc.^*
• Melting point: 55 - 59 °C (Expl.)
• Boiling point: 356.5±32.0 °C 760 mmHg (Calc.)^*
• Flash point: 169.4±25.1 °C (Calc.)^*
• Index of refraction: 1.513 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-iodopropanoate is a chemical compound that belongs to the class of amino acid derivatives, specifically a modified amino acid ester. The structure of this compound includes a propanoate backbone, where the amino group is protected by a tert-butoxycarbonyl (Boc) group. The molecule also features an iodine atom at the 3-position of the carbon chain, which plays a critical role in the compound's reactivity and utility in organic synthesis.

This compound is primarily used as an intermediate in the synthesis of more complex molecules, particularly in the field of medicinal chemistry and peptide synthesis. The presence of the Boc group allows for selective reactions that are useful in peptide bond formation, as the Boc group can be easily removed under acidic conditions to reveal the free amine. This characteristic makes Methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-iodopropanoate a valuable reagent in the synthesis of peptide-based drugs, where the precise introduction of amino acids is essential for creating bioactive peptides with desired properties.

The iodine atom at the 3-position enhances the electrophilicity of the carbon in the adjacent carbonyl group, making the compound reactive in nucleophilic substitution reactions. This reactivity is exploited in various chemical transformations, where the iodine atom can be replaced by other nucleophiles, such as amines or alcohols. This ability to participate in substitution reactions expands the potential applications of Methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-iodopropanoate in the synthesis of diverse organic molecules, including those with potential pharmaceutical applications.

In addition to its use in peptide and drug synthesis, this compound may also play a role in the development of bioconjugates, where amino acid derivatives are linked to other bioactive molecules, such as antibodies or enzymes. The ability to functionalize the compound further via the Boc group or the iodine atom allows for controlled modification of these bioconjugates, which can enhance their stability, specificity, and therapeutic efficacy.

Furthermore, the use of iodine as a functional group in organic synthesis is well-established due to its ability to facilitate electrophilic aromatic substitution reactions and other transformations where halogenation plays a central role. As such, Methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-iodopropanoate can also be considered a building block in the development of various chemical libraries for drug discovery, especially in the search for novel compounds that interact with specific biological targets.

In summary, Methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-iodopropanoate is a valuable intermediate in organic synthesis, particularly in peptide chemistry, medicinal chemistry, and drug development. Its structure allows for selective reactivity due to the protection of the amino group and the presence of an iodine atom, which can be used in a variety of synthetic transformations. This compound’s ability to undergo nucleophilic substitution reactions and its utility in peptide bond formation make it a crucial reagent in the synthesis of bioactive peptides and other complex organic molecules.

References

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