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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
3-Amino-4-methylpentanoic acid is a human metabolite.
Synonyms: beta-Leucine; DL-Homovaline; beta-Aminoisocaproic acid
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Batch number can be found on the product's label following the word 'Batch'.
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.
Batch number can be found on the product's label following the word 'Batch'.
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.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 5699-54-7 |
Formula : | C6H13NO2 |
M.W : | 131.17 |
SMILES Code : | CC(C)C(N)CC(O)=O |
Synonyms : |
beta-Leucine; DL-Homovaline; beta-Aminoisocaproic acid
|
MDL No. : | MFCD00800505 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-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 |
---|---|---|
46% | With sodium hydroxide; water; In isopropyl alcohol; at 28℃; for 24.0h;pH 8.0;Resolution of racemate; Enzymatic reaction; | 1 ml of suspension of penicillin acylase CHIROCLEC-EC ) WAS ADDED to a solution of 500 mg of N-phenylacetylated ss-homovaline 3 (2 mmol) in 3 ml of isopropanol, 7 ML of 10-2 M buffer solution, pH 8, and 2 ml of water. The reaction medium was stirred at 28C and the pH was maintained at pH 8 by means of an autotitrator, by adding a 0.1 N sodium hydroxide solution. After stirring for 24 hours, the reaction medium was centrifuged, making it possible to separate the solution from the enzyme. The solution was concentrated and the aqueous phase was then acidified to pH 2 and extracted with 3 times 10 ml of ethyl acetate. The organic phases were pooled and dried over magnesium sulphate. After evaporation, the residue was purified by flash chromatography (cyclohexane/ethyl ACETATE/FORMIC acid 1/1/0. 01) in order to separate the phenylacetic acid from the substrate (yield = 46%). The aqueous phase was lyophilized and the residue was chromatographed on Dowex 50H RESIN to give the neutral amino acid (yield = 45%). M. P. = 206C. [alpha]20D = +47 (C = 1 ; H20) ; LITT. L : [alpha]20D = +40. 3 (c = 1.02 ; H2O). 13C NMR: delta (D20) : 179.6 (s, COOH), 55. 9 (s, CHNH2), 37. 1 (s, CH2CO2H, 31. 1 (s, (CH3)CH), 18.5 & 18.3 (2S, (CH3)2CH).; 1H NMR:delta (D2O): 3.12 (DDD, 3JH-H=4.3 HZ, 3JH-H=6 HZ, 3JH-H=9.3 HZ, 1H, CHNH2), 2.37 (dd, 3JH-H=4. 3 Hz, 3JH H=16. 8 Hz, 1H of CH2CO2H), 2.19 (dd, 3JH_H=9. 3 HZ, 3JH- IFF 16. 8 HZ, 1H OF CH2CO2M, 1.73 (dq, 3JH-H=6.8 Hz, 3JH-H=6.4 Hz, 1H, (CH3) CH), 0.79 & 0.78 (2d, 3JH-H=6. 8 Hz, 6H, (CH3) 2CH). I. I.R. : (KBR) 3300-2000 (nu OHacid), 3000-2000 (nu NH), 1625 (nu NH2), 1556 (nu COO-carboxylate), 1399 (nu COO-carboxylate). Elemental analysis : Calculated: C 54.94% ; H 9. 99% ; N 10.68% Measured : C 54. 79%; H 10. 02% ; N 10. 78%. (35)-4-METHYL-3-PHENVLACETAMIDONENTANOIC ACID (XI D = +25 (c = 1. 1; CH2Cl2) The enantiomeric excesses of the 4-METHYL-3-PHENYLACETAMIDOPENTANOIC acid were measured on the compound amidated with (R) -naphthylethylamine by HPLC. The enantiomeric excess was greater than 99%. Elution conditions: Macherey-Nagel Nucleosil 50-5 column ; mobile phase: HEXANE/ETOAC ; 2/3. flow rate: 2 ml/min.; detection No. = 265 nm; TR = 7.3 min for (S, R), 15.6 min for (R, R). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sodium carbonate; In water; acetone; at 20℃; | Di-tert-Butyl dicarbonate (243.0 g, 1.1 mol) was added dropwise to a suspension of (R)-3-amino-4-methyl pentanoic acid (commercially available) (133.0 g, 1.0 mol) and Na2C03 (212 g, 2.0 mol) in acetone (1 L) and water (1 L) with stirring at room temperature. The reaction mixture was stirred overnight and the organic solvent was removed under reduced pressure. The residue was diluted with water (1 L) and washed with EtOAc (500 mL x3). The aqueous phase was acidified with 2N HC1 solution to pH=3 and the resulting mixture was extracted with EtOAc (800 mL x3). The combined extracts were washed with brine (800 mL xl), dried (anhydrous Na2S04) and concentrated to give compound (T2) (224.0 g, 97% yield) as an oil, which was used in the next step without further purification. |
97% | With sodium carbonate; In water; acetone; at 20℃; | Compound T2 [0575] B0C2O (243.0 g, 1.1 mol) was added dropwise to a suspension of (R)-3-amino-4- methyl pentanoic acid (commercially available) (133.0 g, 1.0 mol) and Na2C03 (212 g, 2.0 mol) in acetone (1 L) and water (1 L) with stirring at room temperature. The reaction mixture was stirred overnight and the organic solvent was removed under reduced pressure. The residue was diluted with water (1 L) and washed with EtOAc (500 mL x3). The aqueous phase was acidified with 2N HCl solution to pH=3 and the resulting mixture was extracted with EtOAc (800 mL x3). The combined extracts were washed with brine (800 mL xl), dried (Na2S04) and concentrated to give compound (T2) (224.0 g, 97% yield) as an oil, which was used in the next step without further purification. |
97% | With sodium carbonate; In water; acetone; at 18 - 25℃; | Boc2O (243.0 g, 1.1 mol) was added dropwise to a suspension of (R)-3-amino-4-methyl pentanoic acid (commercially available) (133.0 g, 1.0 mol) and Na2CO3 (212 g, 2.0 mol) in acetone (1 L) and water (1 L) with stirring at room temperature. The reaction mixture was stirredovernight and the organic solvent was removed under reduced pressure. The residue was diluted with water (1 L) and washed with EtOAc (500 mL x3). The aqueous phase was acidified with 2N HC1 solution to pH=3 and the resulting mixture was extracted with EtOAc (800 mL x3). The combined extracts were washed with brine (800 mL x 1), dried (Na2SO4) and concentrated to give compound (2) (224.0 g, 97% yield) as an oil, which was used in the next step withoutfurther purification. |