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Ethyl 4-((tert-butoxycarbonyl)amino)-3-oxobutanoate
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CAS No. 67706-68-7
- Cat. No. CS-0151539
- Purity≥95%
- MDL No.MFCD11616704
*For research and further manufacturing use only, not for direct human use.
Structure of 67706-68-7
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General Information
- CAS No. 67706-68-7
- Cat. No. CS-0151539
- Purity ≥95%
- MDL No. MFCD11616704
- Storage 4°C, stored under nitrogen
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₁H₁₉NO₅
- Molecular Weight 245.27
- Synonym(s) TERT-BUTYL 3-(ETHOXYCARBONYL)-2-OXOPROPYLCARBAMATE
- SMILES CCOC(CC(CNC(OC(C)(C)C)=O)=O)=O
Description
Ethyl 4-((tert-butoxycarbonyl)amino)-3-oxobutanoate features a masked α-amino ketone scaffold, enabling direct incorporation into peptide-like architectures. The tert-butoxycarbonyl group provides orthogonal protection for amine functionalities, while the β-keto ester moiety supports facile cyclization and C–C bond formation under mild conditions. This reagent streamlines access to complex heterocyclic frameworks in synthetic medicinal chemistry and natural product synthesis.
Application
Ethyl 4-((tert-butoxycarbonyl)amino)-3-oxobutanoate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to β-amino carbonyl scaffolds. The molecule combines a stable tert-butyl carbamate (Boc) protecting group with an α,β-unsaturated ester motif, facilitating sequential transformations including reduction, alkylation, and cyclization. Its bench-stable nature and compatibility with diverse reaction conditions make it well-suited for peptide-like fragment synthesis and heterocycle construction in medicinal chemistry workflows.
Synthesis
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References
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Baxter, Jenny M.; Steinhuebel, Dietrich; Palucki, Michael; Davies, Ian W. Organic Letters, 2005 , vol. 7, # 2 p. 215 - 218
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Route2
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In-stock
24424-99-5 -
86578-55-4 - ~72%
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In-stock
67706-68-7
References
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Chen, Jie; Fu, Xiao-Gang; Zhou, Ling; Zhang, Jun-Tao; Qi, Xian-Liang; Cao, Xiao-Ping Journal of Organic Chemistry, 2009 , vol. 74, # 11 p. 4149 - 4157
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Route3
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In-stock
1071-46-1 -
18185-77-8
- ~%
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In-stock
67706-68-7
References
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Mazitschek, Ralph; Tallarico, John A.; Maliga, Zoltan; Mitchison, Timothy J. Patent: US2010/152206 A1, 2010 ; Location in patent: Page/Page column 25-26 ;
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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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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Quality Control
Computational Chemistry Data
- TPSA 81.7
- LogP 1.0334
- H_Acceptors 5
- H_Donors 1
- Rotatable_Bonds 5
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Key Words
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