3339-44-4

Basic information

• Product Name: N-ME-VAL-OME HCL
• Synonyms: H-L-MEVAL-OME HCL;H-MEVAL-OME HCL;N-ALPHA-METHYL-L-VALINE-METHYL ESTER HYDROCHLORIDE;N-METHYL-L-VALINE METHYL ESTER HYDROCHLORID;N-METHYL-L-VALINE METHYL ESTER HYDROCHLORIDE;N-ME-VALINE-OME HCL;N-ME-VAL-OME HCL;N-Me-Val-OMe
• CAS NO: 3339-44-4
• Molecular Formula: C₇H₁₆NO₂*Cl
• Molecular Weight: 181.66
• Product Categories: amino acids
• Mol File: 3339-44-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 140-141℃
• Appearance: /Solid
• Storage Temp.: Store at RT.
• CAS DataBase Reference: N-ME-VAL-OME HCL(CAS DataBase Reference)
• NIST Chemistry Reference: N-ME-VAL-OME HCL(3339-44-4)
• EPA Substance Registry System: N-ME-VAL-OME HCL(3339-44-4)

Safety Data

• Hazardous Substances Data: 3339-44-4(Hazardous Substances Data)

Usage

Description

N-ME-VAL-OME HCL, also known as N-Methylvaline Methyl Ester Hydrochloride, is an organic compound that serves as a key reactant in the synthesis of various organic compounds. It is characterized by its unique chemical structure and reactivity, making it a valuable component in the field of organic chemistry.

Uses

Used in Pharmaceutical Industry:
N-ME-VAL-OME HCL is used as a reactant for the synthesis of etrapeptide belamide A, which is a potential therapeutic agent with various pharmacological properties. Its role in the synthesis process is crucial for the development of new drugs and treatments.
Used in Chemical Research:
N-ME-VAL-OME HCL is used as a reactant for the synthesis of 2-?chloro-?1,?3-?dimethyl-?1H-?benzimidazolium hexafluorophosphate (CMBI), a compound with potential applications in chemical research and development. Its versatility as a reactant allows for the exploration of new chemical pathways and the creation of novel compounds with diverse applications.

Upstream product

• 67-56-1 methanol 
• 42417-65-2 Z-MeVal-OH 
• 53363-91-0 2-(N-benzyloxycarbonyl-N-methylamino)-3-methylbutyric acid methyl ester 
• 24164-06-5 methyl (2S)-2-[(tert-butoxycarbonyl)(methyl)amino]-3-methylbutanoate 
• 202273-45-8 (S)-4-Isopropyl-3-methyl-2,2-bis-trifluoromethyl-oxazolidin-5-one 
• 58561-04-9 N-tert-butoxycarbonyl-L-valine methyl ester 
• 2480-23-1 N-methyl-L-valine 
• 13734-41-3 t-Boc-L-valine 
• 45170-31-8 Boc-N-Me-Val-OH 
• 72-18-4 L-valine 
• 6458-35-1 (S)-4-isopropyl-2,2-bis-trifluoromethyl-oxazolidin-5-one 
• 202273-37-8 (S)-3-Chloromethyl-4-isopropyl-2,2-bis-trifluoromethyl-oxazolidin-5-one 

Downstream Products

• 128892-32-0 -N-methyl-L-valine methyl ester 
• 128892-33-1 -N-methyl-L-valine methyl ester 
• 128892-34-2 Z-MeLeu-MeVal-OMe 
• 128892-29-5 Z-D-Val-MeVal-OMe 
• 128892-28-4 N--L-N-methylvaline methyl ester 
• 128892-35-3 Z-D-MeLeu-MeVal-OMe 
• 194933-46-5 (S)-2-[((2S,3R)-3-Benzyloxy-2-tert-butoxycarbonylamino-butyryl)-methyl-amino]-3-methyl-butyric acid methyl ester 
• 445396-25-8 N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-dimethylglycyl-(S)-methylvaline 
• 445396-20-3 methyl N-[(benzyloxy)carbonyl]-(S)-phenylalanyl-dimethylglycyl-(S)-N-methylvalinate 
• 270085-21-7 N-(tert-butyloxycarbonyl)-valyl-valyl-methylvalyl-prolyl-proline benzyl ester 
• 215393-56-9 (S)-1-[(S)-1-((S)-2-{[(S)-2-((S)-2-Dimethylamino-3-methyl-butyrylamino)-3-methyl-butyryl]-methyl-amino}-3-methyl-butyryl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carboxylic acid benzyl ester 
• 194933-47-6 (S)-2-({(2S,3R)-3-Benzyloxy-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-butyryl}-methyl-amino)-3-methyl-butyric acid methyl ester 
• 194933-49-8 (S)-2-[((2S,3R)-3-Benzyloxy-2-{(S)-2-[((2R,4R)-2,4-dimethyl-octanoyl)-methyl-amino]-4-methyl-pentanoylamino}-butyryl)-methyl-amino]-3-methyl-butyric acid 
• 194933-48-7 (S)-2-[((2S,3R)-3-Benzyloxy-2-{(S)-2-[((2R,4R)-2,4-dimethyl-octanoyl)-methyl-amino]-4-methyl-pentanoylamino}-butyryl)-methyl-amino]-3-methyl-butyric acid methyl ester 

Relevant articles and documents

The multicomponent approach to N-methyl peptides: Total synthesis of antibacterial (-)-viridic acid and analogues

Two syntheses of natural viridic acid, an unusual triply N-methylated peptide with two anthranilate units, are presented. The first one is based on peptide-coupling strategies and affords the optically active natural product in 20% overall yield over six steps. A more economical approach with only four steps leads to the similarly active racemate by utilizing a Ugi four-component reaction (Ugi-4CR) as the key transformation. A small library of viridic acid analogues is readily available to provide first SAR insight. The biological activities of the natural product and its derivatives against the Gram-negative bacterium Aliivibrio fischeri were evaluated.

Synthesis and use of 2H-azirin-3-amines as dipeptide synthons

The synthesis of the new 2H-azirin-3-amines ('3-amino-2H-azirines') 11, 20, 28, and 33 as dipeptide synthons is described. The reactions of the starting amides with Lawesson reagent gave the corresponding thioamides, and consecutive treatment with COCl2, 1,4-diazabicyclo[2.2.2]octane (DABCO), and NaN3 led to the desired products. It is shown that these 2H-azirin-3-amines can conveniently be used as building blocks of the dipeptides Aib-(Me)Axx (Axx=alanine, valine), Aib-Homoproline, and Iva-Pro in the synthesis of several model peptides. However, some limitations apply for the synthesis of such 2H-azirin-3-amines. The starting material for the azirine synthesis, the corresponding thioamides, cannot generally be synthesized, and the 2H-azirin-3-amines could not be obtained in all cases from the thioamides prepared.

An efficient synthesis of N-methylamino acids and some of their derivatives

N-Methylamino acid derivatives are obtained in high yield by a stereoselective one-pot procedure from hexafluoroacetone protected amino acids via N-chloromethylation and treatment with triethylsilane/trifluoroacetic acid.