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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.
Synonyms: (S)-β-Hydroxybutanoic acid; L-(+)-3-Hydroxybutyric acid; L-β-Hydroxybutyric acid
 
                
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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'.
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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.
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| CAS No. : | 6168-83-8 | 
| Formula : | C4H8O3 | 
| M.W : | 104.10 | 
| SMILES Code : | C[C@H](O)CC(O)=O | 
| Synonyms : | 
                                (S)-β-Hydroxybutanoic acid; L-(+)-3-Hydroxybutyric acid; L-β-Hydroxybutyric acid
                             | 
| MDL No. : | MFCD00137685 | 
| InChI Key : | WHBMMWSBFZVSSR-VKHMYHEASA-N | 
| Pubchem ID : | 94318 | 
| GHS Pictogram: |   | 
| 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 | 
|---|---|---|
| With bacterial isolate; In aq. phosphate buffer; at 15℃;pH 7.2; | General procedure: The procedure for large scale biotransformation of racemic 3-hydroxybutyronitrile was similar to the general procedure, with the exception of the use of potassium phosphate buffer (0.1 M, pH 7.0, 100 mL) containing 3-hydroxybutyronitrile (85.1 mg, 10 mM). The resulting aqueous solution was basified to pH 12 with aqueous NaOH (2 M) and extracted with ethyl acetate (3 × 100 mL). The aqueous solution was acidified using aqueous HCl (2 M) to pH 2 and extracted with ethyl acetate (3 × 100 mL), dried over MgSO4 and the solvent removed under vacuum. The crude product was subjected to silica gel column chromatography eluted with a mixture of hexane and ethyl acetate (1:1) to give 3-hydroxybutyric acid in 42percent yield (44 mg, 4.23 mmol) as clear oil. The configuration of the corresponding acid was determined by comparing the direction of specific rotation with that of an authentic sample. Enantiomeric excess values were obtained from HPLC analysis using a column of chiral stationary phase and correlated with literature. (R)-enantiomer elutes at 11.94 min, (S)-enantiomer elutes at 12.34 min [34]. 1H NMR (400 MHz, CDCl3) delta = 4.19?4.27 (1H, m), delta = 2.45?2.58 (2H, m), delta = 1.23 (3H, d, J = 6.3 Hz). 13C NMR (400 MHz, CDCl3) delta = 117, 76, 64, 42, 22 [alpha]d25 = +4.0 (c = 2.5, MeOH), and compared with that in the literature [alpha]d25 = +4.1 (c = 2.7, MeOH) [35]. This experiment was performed in triplicate. | 
 [ 6168-83-8 ]
                                                    
                                                    [ 6168-83-8 ]


 [ 124-38-9 ]
                                                    
                                                    [ 124-38-9 ]
 [ 7732-18-5 ]
                                                    
                                                    [ 7732-18-5 ] [ 6168-83-8 ]
                                                    
                                                    [ 6168-83-8 ]
 [ 195006-98-5 ]
                                                    
                                                    [ 195006-98-5 ]

 [ 6168-83-8 ]
                                                    
                                                    [ 6168-83-8 ]
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 22% | With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 2.0h; | To a solution of (S)-3-hydroxybutyrate (0.180 g, 1.73 mmol), HATU (0.602 g, 1.58 mmol), DIEA (1.0 mL, 5.4 mmol) in DMF (3.0 mL) was added a solution of 4-(4-aminophenyl)-N-(4-mophiholinophenyyl)pyrimidin-2-amine (0.500 g, 1.44 mmol) in DMF (1.0 mL). The reaction mixture was stirred at rt for 2 hours, at which time it was quenched with saturated NaHCC>3 (10 mL, aq.), extracted into DCM (3X), and washed with brine (IX). The organic layers were dried with sodium sulfate and concentrated. The product was purified by reverse phase HPLC to afford (S)-3-hydroxy-N-(4-(2-(4- morpholinophenylamino)pyrimidin-4-yl)phenyl)butanamide (0.136 g, 22percent yield) as a light brown solid. (363) 1H-NMR (400MHz, DMSCW6): 10.14 (s, IH), 9.38 (s, IH), 8.44 (d, IH), 8.12 (d, 2H), 7.77 (d, 2H), 7.68 (d, 2H), 7.27 (d, IH), 6.94 (d, 2H), 4.79 (d, IH), 4.11 (m, IH), 3.74 (m, 4H), 3.05 (m, 4H), 2.47 (dd, IH), 2.35 (dd, IH) ), 1.15 (d, 3H); MS (EI) m/z for C24H28N5O3: 434.3 (MH+). | 
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 96% | In ethyl acetate; at 25 - 60℃; | Example 17: Synthesis of N-r(lS)-l-benzyl-2-(KlR)-3-rnethyl-l-r(5R)-4-oxo-5-phenyl-l,3,2- dioxaborolan-2-vnbutyl )amino)-2-oxoethyllpyrazine-2-carboxamide (1-17)[0345] To a solution of (S)-3-hydroxybutyric acid (0.0509 g, 0.489 mmol) in EtOAc (2.0 mL) with an internal temperature of about 60 0C was added N,N',N"-(boroxin-2,4,6-triyltris{ [(lR)-3- methylbutane-1 , l-diyl]imino[(2S)- 1 -oxo-3-phenylpropane- 1 ,2-diyl] } )tripyrazine-2-carboxamide (0.179 g, 0.163 mmol) as a solid. The solution was cooled uncontrolled until the internal temperature was about 25 0C and the solvent was removed by evaporation to yield N-[(lS)-l-benzyl-2-({(lR)-3- methyl-l-[(4S)-4-methyl-6-oxo-l,3,2-dioxaborinan-2-yl]butyl }amino)-2-oxoethyl]pyrazine-2- carboxamide as a white solid (0.213 g, 96%). MS (m/z) in CH3CN: [M+Na] calculated for C23H29BN4NaO5, 475.2; found, 475.2. MS (m/z) in CH3CN: [M-H] calculated for C23H28BN4O5, 451.2; found, 451.1. | 
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 95% | In ethyl acetate; at 25 - 60℃; | Example 8. Synthesis of 2,5-dichloro-N-r2-({(lR)-3-methyl-l-r(4S)-4-methyl-6-oxo-l,3,2- dioxaborinan-2-vpibutyl )amino)-2-oxoethvHbenzamide (1-8)[0335] To a solution of (S)-3-hydroxybutypic acid (0.0598 g, 0.566 mmol) in EtOAc (2.0 mL) with an internal temperature of about 60 °C was added a solution of N,N',N"-{boroxin-2,4,6-tpiyltris[[(lR)- 3-methylbutane-l.l-diyl]imino(2-oxoethane-2,l-diyl)] }tris(2,5-dichlorobenzamide) (0.200 g, 0 195 mmol) in EtOAc (1.0 mL). The solution was cooled uncontrolled until the internal temperature was about 25 0C and the solvent was removed by evaporation to yield 2,5-dichloro-N-[2-({(lR)-3-methyl- l-[(4S)-4-methyl-6-oxo-l,3,2-dioxaborinan-2-yl]butyl}arruno)-2-oxoethyl]benzamide as a white solid (0.225 g, 95percent). 1H NMR (300 MHz, DMSO-d6, delta): 10.45 (s, IH), 9.11 (t, J = 6.0 Hz, IH), 7.65 (m, IH), 7.55 (m, 2H), 4.21 (d, J = 6.0 Hz, 2H), 3.98 - 3.90 (m, IH), 2.51 (m, IH), 2.33 (dd, J1 = 19.2 Hz, J = 2.7 Hz, IH), 2.24 - 2.21 (m, IH), 1.61 - 1.52 (m, IH), 1.33 - 1.19 (m, 2H), 1 07 - 1.04 (m, 3H), 0.84 (m, 6H). MS (m/z) in CH3CN: [M+ Et3N+H] calculated for C24HS9BCl2N3O5, 530.2; found, 5300. MS (m/z) in CH3CN: [M-H] calculated for C18H22BCl2N2O5, 427.1 ; found, 427.1. | 
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 56% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 16.0h; | 5-(9-Isobutyl-6-morpholin-4-yl-8-piperazin-1-yl-9H-purin-2-yl)pyrimidin-2-amine (150 mg, 0.33 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (128 mg, 0.67 mmol), 1-hydroxybenzotriazole (45 mg, 0.33 mmol), and (S)-3-hydroxybutyric acid (70 mg, 0.67 mmol) were dissolved in dimethylformamide (5 ml) and the resulting mixture was stirred for 16 hours. The solvent was evaporated under reduced pressure and then the residue was purified by preparative HPLC (column, NOMURA Develosil Combi-RP-5; mobile phase, acetonitrile/water/formic acid) to give the title compound (97 mg, 56percent) as a white solid.1H-NMR (CDCl3) delta: 0.88 (3H, s), 0.90 (3H, s), 1.26 (3H, d, J=6.3 Hz), 2.35-2.56 (3H, m), 3.21 (2H, t, J=5.0 Hz), 3.26 (2H, t, J=5.0 Hz), 3.64 (2H, t, J=5.0 Hz), 3.81-3.85 (6H, m), 3.92 (2H, d, J=7.6 Hz), 4.25-4.28 (5H, m), 5.22 (2H, s), 9.24 (2H, s). | 
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 48% | With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 40℃; for 16.0h; | 5-{9-Isobutyl-8-[(3S)-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine (230 mg, 0.5 mmol), dicyclohexylcarbodiimide (160 mg, 0.77 mmol), 1-hydroxybenzotriazole (70 mg, 0.51 mmol), and (S)-3-hydroxybutyric acid (107 mg, 1.0 mmol) were dissolved in dimethylformamide (5 ml) and the resulting mixture was stirred at 40° C. for 16 hours. The solvent was evaporated under reduced pressure and then the residue was purified by preparative HPLC (column, NOMURA Develosil Combi-RP-5; mobile phase, acetonitrile/water/formic acid) to give the title compound (131 mg, 48percent) as a white solid.1H-NMR (CDCl3) delta: 0.90 (6H, t, J=6.6 Hz), 1.24-1.27 (3H, m), 1.40 (1.5H, d, J=6.8 Hz), 1.48 (1.5H, d, J=6.8 Hz), 2.28-2.64 (4H, m), 3.01-3.15 (3H, m), 3.27 (1H, d, J=12.2 Hz), 3.42 (1H, d, J=12.2 Hz), 3.54-3.56 (0.5H, m), 3.72-3.74 (0.5H, m), 3.84-3.96 (6H, m), 4.18-4.27 (6H, m), 4.58-4.61 (0.5H, m), 4.92-4.95 (0.5H, m), 5.49 (2H, s), 9.23 (2H, s). | 
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 61% | With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 40℃; for 16.0h; | 5-{9-Isobutyl-8-[(3R)-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine (230 mg, 0.5 mmol), dicyclohexylcarbodiimide (160 mg, 0.77 mmol), 1-hydroxybenzotriazole (70 mg, 0.51 mmol), and (S)-3-hydroxybutyric acid (107 mg, 1.0 mmol) were dissolved in dimethylformamide (5 ml) and the resulting mixture was stirred at 40° C. for 16 hours. The solvent was evaporated under reduced pressure and then the residue was purified by preparative HPLC (column, NOMURA Develosil Combi-RP-5; mobile phase, acetonitrile/water/formic acid) to give the title compound (167 mg, 61percent) as a white solid.1H-NMR (CDCl3) delta: 0.90 (6H, t, J=6.6 Hz), 1.24-1.27 (3H, m), 1.39 (1.5H, d, J=6.8 Hz), 1.47 (1.5H, d, J=6.8 Hz), 2.27-2.57 (4H, m), 2.96-3.20 (3H, m), 3.29 (1H, d, J=12.2 Hz), 3.42 (1H, d, J=12.2 Hz), 3.54-3.56 (0.5H, m), 3.71-3.74 (0.5H, m), 3.84-3.96 (6H, m), 4.18-4.27 (6H, m), 4.58-4.61 (0.5H, m), 4.92-4.95 (0.5H, m), 5.50 (2H, s), 9.22 (2H, s). | 
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 81% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 21.0h; | A methylene chloride (3 ml) solution of 5-{9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-8-piperazin-1-yl-9H-purin-2-yl}pyrimidin-2-amine (94 mg, 0.21 mmol), (3S)-<strong>[6168-83-8]3-hydroxybutanoic acid</strong> (24 mg, 0.23 mmol), 1-hydroxybenzotriazole (28 mg, 0.21 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (60 mg, 0.31 mmol), and triethylamine (44 mul, 0.31 mmol) was stirred at room temperature for 21 hour. Chloroform and saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture and the resulting mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and, after filtration, the filtrate was concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (methylene chloride:methanol=95:5) to give an amorphous substance. Ethyl acetate-hexane was added to the resulting amorphous substance, the resulting mixture was solidified, and the solid was collected by filtration and dried to give the title compound (91 mg, 81percent) as a powder.1H-NMR (CDCl3) delta: 0.89 (6H, d, J=6.8 Hz), 1.26 (3H, d, J=6.3 Hz), 1.40 (3H, d, J=6.8 Hz), 2.33-2.58 (3H, m), 3.16-3.29 (4H, m), 3.42-3.55 (1H, m), 3.59-3.72 (3H, m), 3.75-3.87 (4H, m), 3.99-4.13 (2H, m), 4.21-4.31 (2H, m), 5.03-5.21 (3H, m), 5.29-5.45 (1H, m), 9.24 (2H, s). | 
 [ 6168-83-8 ]
                                                    
                                                    [ 6168-83-8 ]

 [ 1222104-55-3 ]
                                                    
                                                    [ 1222104-55-3 ]| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 50% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; for 15.0h; | (S)-<strong>[6168-83-8]3-hydroxybutanoic acid</strong> (39 mg, 0.38 mmol), hydroxybenzotriazole hydrate (58 mg, 0.38 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (72 mg, 0.38 mmol), dimethylformamide (5 ml), and triethylamine (161 mul) were added to 5-[6-morpholin-4-yl-8-piperazin-1-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-amine trifluoroacetate (200 mg, 0.29 mmol) and the resulting mixture was stirred for 15 hours. The reaction mixture was partitioned with ethyl acetate and saturated aqueous sodium bicarbonate solution, the organic layer was dried over magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (chloroform:methanol=19:1) to give the title compound (80 mg, 50percent) as a white solid.1H-NMR (CDCl3) delta: 1.26 (3H, d, J=6.3 Hz), 2.38 (1H, dd, J=16.3, 9.5 Hz), 2.53 (1H, dd, J=16.6, 2.3 Hz), 3.17-3.24 (4H, m), 3.63-3.80 (4H, m), 3.84-3.89 (5H, m), 4.27 (4H, brs), 4.73 (2H, q, J=8.4 Hz), 9.23 (2H, s). |