24164-06-5

Basic information

• Product Name: methyl N-(tert-butoxycarbonyl)-N-methylvalinate
• CAS NO: 24164-06-5
• Molecular Formula: C₁₂H₂₃NO₄
• Molecular Weight: 245.3153
• Mol File: 24164-06-5.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 293.5°C at 760 mmHg
• Flash Point: 131.3°C
• Density: 1.015g/cm³
• Vapor Pressure: 0.00172mmHg at 25°C
• Refractive Index: 1.448
• CAS DataBase Reference: methyl N-(tert-butoxycarbonyl)-N-methylvalinate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl N-(tert-butoxycarbonyl)-N-methylvalinate(24164-06-5)
• EPA Substance Registry System: methyl N-(tert-butoxycarbonyl)-N-methylvalinate(24164-06-5)

Safety Data

• Hazardous Substances Data: 24164-06-5(Hazardous Substances Data)

Upstream product

• 72-18-4 L-valine 
• 6306-52-1 L-valine methylester hydrochloride 
• 45170-31-8 Boc-N-Me-Val-OH 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 610800-51-6 N-methyl-N-4-nitrophenylsulfonyl-L-valine methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 35016-37-6 N-methyl-L-valine methyl ester 
• 13734-41-3 t-Boc-L-valine 
• 186581-53-3 diazomethane 
• 58561-04-9 N-tert-butoxycarbonyl-L-valine methyl ester 

Downstream Products

• 45170-31-8 Boc-N-Me-Val-OH 
• 18944-00-8 N-methyl-valine hydrochloride 
• 1174764-12-5 (2S,4R)-2-methyl-4-[({2-[(3R)-4-methyl-3-{methyl[(2S,3S)-3-methyl-2-({[(2R)-1-methylpiperidin-2-yl]carbonyl}amino)pentanoyl]amino}pentyl]-1,3-thiazol-4-yl}carbonyl)amino]-5-phenylpentanoic acid 
• 1219930-75-2 methyl (2S,4R)-2-methyl-4-[({2-[(3R)-4-methyl-3-{methyl[(2S,3S)-3-methyl-2-({[(2R)-1-methylpiperidin-2-yl]carbonyl}amino)pentanoyl]amino}pentyl]-1,3-thiazol-4-yl}carbonyl)amino]-5-phenylpentanoate 
• 251320-63-5 (S)-tert-butyl (1-hydroxy-3-methylbutan-2-yl)(methyl)carbamate 
• 1268345-13-6 L-Val-N-Me-L-Val-N-Me-L-Phe-Dpy 
• 1268345-12-5 N-Boc-L-Val-N-Me-L-Val-N-Me-L-Phe-Dpy 

Relevant articles and documents

On the selective N-methylation of BOC-protected amino acids

(Chemical Equation Presented) The selective N-methylation of BOC-protected valine 1a with MeI and NaH in THF (i.e., in the presence of a free carboxyl group) has been attributed to the protection of the carboxylate by chelation to Na+. An alternative mechanism, involving the formation of the carbene intermediate generated from MeI and its insertion into the N-H bond, has been ruled out by isotopic labeling. 2009 American Chemical Society.

Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes

Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.

Improved Total Synthesis of Tubulysins and Design, Synthesis, and Biological Evaluation of New Tubulysins with Highly Potent Cytotoxicities against Cancer Cells as Potential Payloads for Antibody-Drug Conjugates

Improved, streamlined total syntheses of natural tubulysins such as V (Tb45) and U (Tb46) and pretubulysin D (PTb-D43), and their application to the synthesis of designed tubulysin analogues (Tb44, PTb-D42, PTb-D47-PTb-D49, and Tb50-Tb120), are described.