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Batch number can be found on the product's label following the word 'Batch'.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 2480-23-1 |
Formula : | C6H13NO2 |
M.W : | 131.17 |
SMILES Code : | CC(C)[C@@H](C(O)=O)NC |
Synonyms : |
N-Methyl-L-valine
|
MDL No. : | MFCD00037754 |
InChI Key : | AKCRVYNORCOYQT-YFKPBYRVSA-N |
Pubchem ID : | 444080 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H319 |
Precautionary Statements: | P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | (2S)-3-Methyl-2-methylamino-butanoic acid (5 g, 38.12 mmol) is added to a stirring solution of sodium hydroxide (76.2 mL of 1 M, 76.24 mmol). After complete dissolution, sodium carbonate (2.1 g, 19.82 mmol) is added followed by methyl chloroformate (3.18 mL, 41.17 mmol) at 0C over 40 minutes. The reaction mixture is stirred at rt for 4 hours, and then washed with diethyl ether (2x 75 ml). The aqueous layer is cooled to 0C, acidified to pH 1 -2 and extracted with CH2Cl2. The organic phase is dried over MgS04, filtered and concentrated to dryness to give the title compound (2S)-2- [methoxycarbonyl(methyl)amino]-3-methyl-butanoic acid (5.12g, 71%) as a clear oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; In water; acetone; at 40℃; for 1h; | General procedure: Samples of each 0.4 mg of 1 and 2 were hydrolyzed by heating in 1 ml 6 N HCl for 24 h at 110 C. After cooling, the solution was evaporated to dryness and the residue redissolved in H2O (50 μL). To each of these hydrolyzate solutions, or to a solution of the reference amino acid (50 μL; 50 mM), a solution of FDAA (Marfey’s reagent, N-(2,4-dinitro-5-fluorophenyl)-l-alaninamide) in acetone (100 μL of 1% (w/v) solution) was added. After addition of NaHCO3 solution (20 μL; 1 M), the mixture was incubated for 1 h at 40 C. The reaction was stopped by addition of HCl (10 μL; 2 M), the solvents were evaporated, and the residue was redissolved in acetonitrile (1 ml). An aliquot of this solution (20 μL) was analyzed by HPLC (Phenomenex Luna C18, 250 4.6 mm, 5 μm; solvents: A is H2O + 0.05% HCOOH, B is MeOH + 0.05% HCOOH; linear gradient from 10% B in A at t = 0 min to 90% B in A within 20 min; 25 C; 300 μL min-1). Configuration of the amino acid units were determined by comparing the chromatograms with those of derivatives of commercially available amino acids. The retention times (min) were as follows: l-Val (15.1), d-Val (16.9), N-Me-l-Val (16.0), N-Me-d-Val (17.0), l-Phe (16.4), d-Phe (18.1), N-Me-l-Phe (15.9), and N-Me-d-Phe (11.6). 26 In independent experiments, all 1/2-derived amino acids were shown to have the l-configuration. | |
With sodium hydrogencarbonate; In water; at 40℃; for 1.5h; | Compounds 1 (1.0 mg) and 2 (1.4 mg) were dissolved in 6 N HCl (1 mL), and heated at 110 C for18 h. After cooling to room temperature, the hydrolysates were dried under reduced pressure and resuspended into 100 μL of H2O.Then they were treated with 1 M NaHCO3 (25 μL), and reacted with100 μL of 1% (w/v) FDAA in acetone at 40 C for 1.5 h. After cooling to room temperature, the mixture was added with 1 M HCl (25 μL) to neutralize and terminate the reaction. MeOH was then added to the quenched reaction to afford a total volume of 500 μL; 10 μL of each hydrolysate derivatization reaction was used for HPLC analysis using an Agilent C18 column (150 × 4.6 mm,5 μM) with a solvent gradient from 15% to 45% solvent B (solvent A: CH3COOH/H2O, 0.05/99.95,solvent B: CH3CN) over the course of 30 min and UV detection at 340 nm at a flow rate of 1 mL/min.Similarly, 10 μL of the standard amino acids in H2O (4 μM) were added to 1 M NaHCO3 (20 μL) and each mixture was treated with 1% (w/v) FDAA (50 μL) for 1.5 h at 40 C. Derivatization reactions were terminated with 1 M HCl (20 μL) and diluted to a total volume of 500 μL with MeOH. Of these standard amino acid derivatization reactions, 10 μL was subjected to HPLC analysis and used as structural standards in the elucidation of structures 1 and 2. | |
With sodium hydrogencarbonate; In methanol; water; acetone; at 40℃; for 1h; | To a solution of compound 1 (0.5 mg, 1.21 μmol) in MeOH (500 μL) was added 12 M HCl (500 μL). The mixture was heated at 100 C for 17 h. The mixture was cooled to room temperature and neutralized with 12 M NaOH solution (500 μL). The resulting aqueous amino acid containing solution was treated by addition of 100 μL of a 1% (w/v) solution of Nα-(5-fluoro-2,4-dinitrophenyl)-L-alaninamide (FDAA) in acetone, 1 M NaHCO3 (50 μL) and H2O (100 μL). The mixture was heated at 40 C for 1 h, then cooled to room temperature, and neutralized with 1 M HCl (50 μL) to give the sample for the analysis. Aliquots (10 μL) of the sample were then analyzed by HPLC with an ODS column using an elution system consisting of solvent A (0.1% TFA/10% MeCN in H2O) and solvent B (0.1% TFA/90% MeCN in H2O). The sample was eluted using a linear gradient of 0% to 10% over the course of 10 min, then 10% to 50% over the course of 20 min, and finally 50% to 100% over the course of 15 min. The flow rate was kept constant at 1 mL/min, and UV detection was employed at 340 nm. Amino acid standards (<strong>[2480-23-1]N-methyl-L-valine</strong> and N-methyl-DL-valinewere prepared by dissolving 50 μg of amino acids in H2O (50 μL) followed by treatment as above using a 1% solution (50 μL) of FDAA in acetone, 1 M NaHCO3 (25 μL) and 1 M HCl (25 μL) for neutralization. The mixture was then processed for HPLC in a fashion similar to that used for sample hydrolysate analyses. The retention times for FDAA derivatives of N-methyl-D-valine and <strong>[2480-23-1]N-methyl-L-valine</strong> were 32.5 and 31.1 min, respectively. The <strong>[2480-23-1]N-methylvaline</strong> fragment in compound 1 was assigned as N-methyl-L-Val (tR 31.3 min). |