13211-31-9

Basic information

• Product Name: tert-Butyl L-valinate
• Synonyms: D-VALINE-OTBU HCL;D-VALINE-T-BUTYL ESTER HYDROCHLORIDE;H-D-VAL-OTBU HCL;Val-OtBu HCl;L-VALINE T-BUTYL ESTER HCL;H-D-Val-OBut·HCl;H-Val-OButCl;L-Valine 1,1-dimethylethyl ester
• CAS NO: 13211-31-9
• Molecular Formula: C₉H₁₉NO₂
• Molecular Weight: 173.25
• EINECS: 236-180-4
• Product Categories: Amino Acids Derivatives;Amino Acids;Valine [Val, V];Amino Acids and Derivatives;Amino Acid Derivatives;Amino hydrochloride
• Mol File: 13211-31-9.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 201.7 °C at 760 mmHg
• Flash Point: 72.1 °C
• Appearance: /
• Density: 0.936 g/cm³
• Vapor Pressure: 0.304mmHg at 25°C
• Refractive Index: 1.441
• Storage Temp.: -15°C
• PKA: 7.91±0.33(Predicted)
• CAS DataBase Reference: tert-Butyl L-valinate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl L-valinate(13211-31-9)
• EPA Substance Registry System: tert-Butyl L-valinate(13211-31-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 13211-31-9(Hazardous Substances Data)

Usage

General Description

Tert-butyl L-valinate is an organic compound that is used in the synthesis and production of pharmaceuticals, flavors, and fragrances. It is a derivative of L-valine, an essential amino acid, and is commonly used as a chiral building block in the preparation of various chemical compounds. Tert-butyl L-valinate is known for its ability to improve the stability, solubility, and bioavailability of active pharmaceutical ingredients, making it a valuable ingredient in pharmaceutical formulations. Additionally, it is also used as a flavoring agent in the food industry, adding a sweet, fruity note to a variety of products.

InChI:InChI=1/C9H19NO2/c1-6(2)7(10)8(11)12-9(3,4)5/h6-7H,10H2,1-5H3/t7-/m0/s1

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 640-68-6 D-Val-OH 
• 87670-16-4 3-Methyl-2-oxo-butyric acid tert-butyl ester 
• 13518-40-6 t-butyl D-valinate hydrochloride 
• 81629-64-3 α-Azido-β-methylbutansaeure-methylester 
• 137524-80-2 (R)-3-methyl-2-(2,2,2-trifluoroacetamido)butanoic acid 
• 142026-07-1 (R)-t-butyl 2-azido-3-methylbutanoate 
• 104-15-4 toluene-4-sulfonic acid 
• 115-11-7 isobutene 
• 72-18-4 L-valine 
• 1245735-69-6 Fms-Val-OtBu 
• 65538-67-2 2,2,2-trichloroethoxycarbonyl-L-valine tert.-butyl ester 
• 13518-40-6 L-valine tert-butylester hydrochloride 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 

Downstream Products

• 14470-31-6 (S)-tert-butyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-methylbutanoate 
• 131400-76-5 Nps-L-Val-OBu^t 
• 131400-77-6 Nps-L-Ala-L-Ala-L-Val-OBu 
• 131400-74-3 Nps-L-Ala-D-Ala-L-Val-OBu^t 
• 129943-49-3 (S)-3-Methyl-2-[(S)-3-phenyl-2-((E)-3-pyridin-3-yl-allyloxycarbonylamino)-propionylamino]-butyric acid tert-butyl ester 
• 99744-63-5 N-<2-(Triphenylphosphonio)isopropyloxy>-L-phenylalanyl-L-valin-tert-butylester-chlorid 
• 145147-68-8 Aloc-Phe-Val-OtBu 
• 139404-87-8 N-benzylidene (S)-valine tert-butyl ester 
• 89656-79-1 N-(2-carbomethoxy-1-cyclohexen-1-yl)-(S)-valine tert-butyl ester 
• 104316-13-4 2-(1-tert-butoxycarbonyl-2-methyl-propylamino)-cyclohex-1-enecarboxylic acid ethyl ester 
• 193810-42-3 (R)-3-Methyl-2-(4-vinyl-benzenesulfonylamino)-butyric acid tert-butyl ester 
• 927438-78-6 2-[2-(benzyloxycarbonyl-methyl-amino)-3-phenyl-propionylamino]-3-methyl-butyric acid tert-butyl ester 
• 143092-96-0 t-butyl 2-(S)-[N-[[N-[1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)pyridine-3carbonyl]amino]acetyl]amino]-3-methylbutylate 
• 26061-29-0 (S)-benzyl 2-((S)-1-tert-butoxy-3-methyl-1-oxobutan-2-ylcarbamoyl)pyrrolidine-1-carboxylate 

Relevant articles and documents

An improved lanthanum catalyst system for asymmetric amination: Toward a practical asymmetric synthesis of AS-3201 (ranirestat)

(Chemical Equation Presented) A catalytic asymmetric amination with a lanthanum/amide complex was significantly improved. The use of lanthanum nitrate hydrate in place of lanthanum triisopropoxide made the process reproducible, scalable, and cost-effective. The development of a ternary catalytic system of La/ligand/amine was a key to high ee and catalytic turnover. A 100 g scale reaction was performed to showcase a practical synthesis of a key intermediate for AS-3201, a highly potent aldose reductase inhibitor.

Synthesis of Dipeptides by Boronic Acid Catalysis

We have found that a boronic acid catalyzed amidation of an N -hydroxy amino acid methyl ester with amino acid tert -butyl esters gave N -hydroxy dipeptide derivatives in good yields without any racemization. The protecting groups on the nitrogen atom could be easily removed by heterogeneous hydrogenation conditions.

Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids

We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C-H acetoxylation of aryl allyl ether, amine, and amino acids with the retention of a labile allyl moiety. Mechanistically, the reaction proceeds through a distinct double-bond isomerization from the allylic to the vinylic position followed by intramolecular carboxypalladation and the β-hydride elimination pathway. For the first time, C-H oxidation of N-allyl-protected amino acids to furnish five-membered heterocycles through 1,3-syn-addition is established with excellent diastereoselectivity.

Synthesis of a leopolic acid-inspired tetramic acid with antimicrobial activity against multidrug-resistant bacteria

The increasing emergence of multidrug-resistant pathogens is one of the biggest threats to human health and food security. The discovery of new antibacterials, and in particular the finding of new scaffolds, is an imperative goal to stay ahead of the evolution of antibiotic resistance. Herein we report the synthesis of a 3-decyltetramic acid analogue of the ureido dipeptide natural antibiotic leopolic acid A. The key step in the synthetic strategy is an intramolecular Lacey-Dieckmann cyclization reaction of a linear precursor to obtain the desired 3-alkyl-substituted tetramic acid core. The synthesized analogue is more effective than the parent leopolic acid A against Gram-positive (Staphylococcus pseudintermedius) and Gram-negative (E. coli) bacteria (MIC 8 μg/mL and 64 μg/mL, respectively). Interestingly, the compound shows a significant activity against Staphylococcus pseudintermedius strains expressing a multidrug-resistant phenotype (average MIC 32 μg/mL on 30 strains tested). These results suggest that this molecule can be considered a promising starting point for the development of a novel class of antibacterial agents active also against resistant strains.