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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.
β-Alanine is a non-specific endogenous agonist at the inhibitory glycine receptor.
Synonyms: 2-Carboxyethylamine; 3-Aminopropanoic acid; beta-Alanine
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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.
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CAS No. : | 107-95-9 |
Formula : | C3H7NO2 |
M.W : | 89.09 |
SMILES Code : | NCCC(O)=O |
Synonyms : |
2-Carboxyethylamine; 3-Aminopropanoic acid; beta-Alanine
|
MDL No. : | MFCD00008200 |
InChI Key : | UCMIRNVEIXFBKS-UHFFFAOYSA-N |
Pubchem ID : | 239 |
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 |
---|---|---|
95.4% | at 60℃; for 5 h; | In a 250 mL reaction flask,Add 180 mL of chloroform,30 g of β-alanine (0.337 mol)37.8 g of acetic anhydride (0.371 mol),Heating up to 60 ,Reaction for 5 hours,Sampling ninhydrin does not develop color,Cooling to 4 ,Stirring for 1 hour,Filter to get solid,Dried to give the product (I) 42 g,The yield was 95.4percentHPLC purity ≥99.3percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.7% | at 50℃; for 5 h; | In a 1000 mL reaction flask,360 mL of toluene was added,120 g beta-alanine (1.348 mol)111.2 g of acetyl chloride (1.417 mol)Heating up to 50 ,Reaction for 5 hours,Sampling ninhydrin does not develop color,Cooling to -3 ,Stirring for 1 hour,Filter to get solid,Dried to give 169.0 g of product (I)The yield was 95.7percent and the HPLC purity was ≥99.3percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.4% | at 45℃; for 3 h; | In a 500 mL reaction flask,Adding dichloromethane to 360 mL,60 g of β-alanine (0.674 mol)48.5 g acetic acid (0.808 mol),Heating up to 45 ,Reaction for 3 hours,Sampling ninhydrin does not develop color,Cooling to 4 ,Stirring for 1 hour,Filter to get solid,Dried to give 82.5 g of product (I)The yield was 93.4percentHPLC purity ≥99.3percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With acetic anhydride In sodium hydrogencarbonate; acetonitrile | Example 19 Preparation of N-Acetyl-β-alanine(4a) To a solution of β-alanine (2,25 g, 25 mmol) in aq. NaHCO3(15 mL) was added acetonitrile (15 mL) and acetic anhydride (2.55 g, 25 mmol). The reaction mixture was stirred at room temperature for 3 h. Acetic anhydride (2.55 g, 25 mmol) was added and after 2 h and pH was adjusted to 4-5 by addition of NaH2PO4. The product was extracted into EtOAc (3*50 mL), dried (Na2SO4), and evaporated to dryness under vacuum to afford 1.96 g (60percent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With acetic acid; at 100℃; for 3h; | Add <strong>[117-21-5]3-chlorophthalic anhydride</strong> (365 mg, 2.0 mmol) and aminopropionic acid (190 mg, 2.1 mmol) to glacial acetic acid(10 mL), heated to 100 C for 3 h. The reaction was quenched with water (10 mL), and the pH of the solution was adjusted to NaOH solution (0.1 mol/L).6-8. Filtered and dried to give a yellow solid 425mg, LC-MS and 1H-NMR confirmed the expected intermediate compound, yield 96.0%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; | b-Alanine (8.9 g, 100 mmol) was dissolved in 10 mL of water. Maleic anhydride (9.8 g, 100 mmol) was added all at once and the mixture was stirred for 4 hours at ambient temperature. After completion of the reaction, the mixture was filtered and the white power obtained was washed with water (3'10 mL) followed by anhydrous ethanol (3'10 ml), and then anhydrous ether (3'10 mL). After drying, 11.6 g (69%) of the maleamic acid was obtained. 1H NMR (300 MHz, D2O) d 2.45 (t, J=6.4 Hz, 2H), 3.32 (t, J=6.4 Hz, 2H), 6.06 (d, J=12.4 Hz, 1H), 6.26 (d, J=12.4 Hz, 1H); HRMS(FAB) calcd for C7H10NO5 (M+H+) 188.0559, found 188.0558. | |
In water; | EXAMPLE 1 Preparation of Maleamic Acid of beta-Alanine beta-Alanine (8.9 grams (g), 100 millimole (mmol)) was dissolved in 10 milliliter (ml) of H2 O. Maleic anhydride (9.8 g, 100 mmol) was added all at once and the mixture was stirred vigorously for four (4) hours at ambient temperature. After completion of the reaction, the mixture was filtered and the white powder obtained was washed with several volumes of H2 O followed by anhydrous ethanol, and then anhydrous ether. After drying, 11.5 g of the maleamic acid was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 4Production of Cs-1O1150 mg of the starting product O-<strong>[121584-52-9]acetyl-CsA-aldehyde</strong> was produced according to the instructions by J. Liu et al. (Anal. Biochem 2006, 356, 100-107) and then mixed with 250 mg H-β-Ala-OH in 30 ml methanol. After mixing for 10 minutes, 8.5 mg NaBH3CN, dissolved in 500 μl methanol, was added and stirring was carried out overnight. After lowering the pH to approximately 1.5 with HCl, the methanol was evaporated under vacuum and the residue was taken up in saline solution and the obtained mixture extracted three times with AcOEt. Then, it was washed with 5% KHSO4 solution, saturated NaHCO3 solution and saline solution. After drying over MgSO4 and filtering, drying was carried out under high vacuum. The residue was then taken up in a mixture, consisting of 15.4 μl AcOH, 104 mg HATU and 145 μl DIPEA, and 1 ml DMF. After mixing for two hours at room temperature, AcOEt was added and the mixture was washed twice successively with saturated NaHCO3, 5% KHSO4 and saline solution. After drying with MgSO4 and filtering, the solvent was evaporated under vacuum. The residue was taken up in 3 ml THF, mixed with 3 ml 0.2 M LiOH, and stirred for 4 hours. After acidification to a pH of approximately 1.5 with HCl, the product was able to be isolated by means of preparative HPLC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure for the preparation of compound 5: The beta-amino acid (1.2 mmol, 1.2 equiv) and the nitro-aldehyde (1.0 mmol, 1.0 equiv.) were dissolved in 20 ml ethanol-water (2:1). The solution was allowed to stand at room temperature for half an hour. The isocyanide (1.0 mmol, 1.0 equiv.) was added to the previous solution and the resulting mixture was stirred at room temperature for 20 h, when the reaction appeared complete by TLC (CH2Cl2:MeOH 98:2), Fe powder (1 mmol) and solid NH4Cl (8-10 equiv.) were added. The reaction mixture was stirred at 80 0C for 16 h. Then it was cooled, filtered through a celite pad and extracted with ethyl acetate (3×30 mL). The extract was washed with brine (30 mL) and dried (sodium sulphate); the solvent was evaporated to give a crude product. This was purified by column chromatography over silica gel (60-120 mesh) using DCM in 5% methanol as an eluent, when 5a was isolated as a light yellow solid. The compounds 5b-h were prepared accordingly. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With sodium methylate; In methanol;Reflux; | A mixture of 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (185 mg, 0.55 mmol), beta-alanine (489 mg, 5.5 mmol) in 0.5 M NaOMe in MeOH solution (8.8 mL, 4.4 mmol) was refluxed overnight. After cooled, the reaction mixture was concentrated and residue was dissolved in water (80 mL). It was acidified by 1 N HC1 solution to pH ca. 3-4. Resulting gummy solid was collected by filtration, rinsed with water and then dissolved in EtOAc. The organic solution was dried over MgSO/t, filtered and concentrated to provide the title compound (173 mg, 0.49 mmol) as an off-white solid in 89% yield. LC-MS ESI-: 351.14 (M-l) |
Tags: H-β-Ala-OH | 2-Carboxyethylamine | Aliphatic Chain Hydrocarbons | Non-protein Amino Acid | Carboxylic Acids | Organic Building Blocks | Amino Acids | 107-95-9
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