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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.
5,5-Dimethyl-2,4-oxazolidinedione is a cathepsin K inhibitor, it's an anticonvulsant.
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| CAS No. : | 695-53-4 |
| Formula : | C5H7NO3 |
| M.W : | 129.11 |
| SMILES Code : | O=C(N1)OC(C)(C)C1=O |
| MDL No. : | MFCD00005379 |
| InChI Key : | JYJFNDQBESEHJQ-UHFFFAOYSA-N |
| Pubchem ID : | 3081 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H302-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.

[ 695-53-4 ]
[ 4725-34-2 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 22% | With sodium; In tetrahydrofuran; for 3h;Reflux; | 5,5-Dimethyloxazolidine-2,4-dione (0.15 g, 1.16 mmol) and sodium (catalytic amount) were added to a stirred solution of 4-methylbenzenesulfonyl chloride (0.17 g, 0.89 mmol) in dry THF (3 mL). The resulting mixture was refluxed for 3h and the reaction progress was followed by TLC. After the addition of DCM (15 mL) to the flask, the mixture was filtered and the solvents were removed. The resulting residue was purified by recrystallization from DCM-light petroleum to give 4h as white crystals (22%); m.p. 119-121C; numax 3049, 2971, 1811, 1772, 1587, 1389, 1300, 1172 cm-1; 1H-NMR delta 1.56 (6H, s, CH3), 2.50 (3H, s, ArCH3), 7.43 (2H, d, J=8.4, ArH), 8.06 (2H, d, J=8.4, ArH); 13C-NMR delta 21.9, 23.6, 83.4, 128.8, 130.3, 133.7, 147.3, 148.1, 170.8; MS-EI m/z 283 (M+); Anal. calcd for C12H13NO5: C 50.88, H 4.62, N 4.94; found C 50.95, H 4.68, N 4.88. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| applying a pharmaceutically effective amount of a cationic derivative of Minoxidil to said skin, said cationic derivative of Minoxidil formed by mixing solutions of Minoxidil with an organic acid selected from the group consisting of; ... 3,4-dihydroxybenzoic acid (also known as protocatechuic acid); 2,3,4-trihydroxybenzoic acid; 3,4,5-trihydroxybenzoic acid (also known as gallic acid); 5-nitro-2-furoic acid; 5,5-dimethyloxazolidine-2-4-dione (also known as dimethadione); and | ||
| ...cally effective amount of a cationic derivative of Minoxidil to a positive donor electrode of an iontophoresis apparatus having a negative receiver electrode, said cationic derivative of Minoxidil formed by mixing solutions of Minoxidil with an organic acid selected from the group consisting of: ... 3,4-dihydroxybenzoic acid (also known as protocatechuic acid); 2,3,4-trihydroxybenzoic acid; 3,4,5-trihydroxybenzoic acid (also known as gallic acid); 5-nitro-2-furoic acid; and 5,5-dimethyloxazolidine-2-4-dione (also known as dimethadione); | ||
| As the compound represented by the formula (XXIV), there are given for example acid imides corresponding to the compounds represented by the foregoing formula (XXIII) and the compounds described below: ... 5,5-Dimethyl-4-thioxo-2-oxazolidinone 5,5-Dimethyl-2,4-thiazolidinedione 2-Thioxo-4-imidazolidinone 2,4-Imidazolidinedione 5,5-Dimethyl-2,4-oxazolidinedione 5,5-Dimethyl-2-thioxo-4-imidazolidinone 5,5-Dimethyl-2,4-imidazolidinedione 5,5-Dimethyl-2-thioxo-4-thiazolidinone ... |
| Consequently, the purity of purified 5,5-dimethyl-2,4-oxazolidinedione was 99.3%; 5,5-dimethyl-2,4-oxazolidinedione was 11.2 g, 2-hydroxyisobutyric acid amide was 7.7 g, methyl carbamate was 1.0 g in the filtrate; 5,5-dimethyl-2,4-oxazolidinedione was 8.1 g, 2-hydroxyisobutyri c acid amide was 1.7 g, and methyl carbamate was 0.2 g in the wash liquid. The net yield of 5,5-dimethyl-2,4-oxazolidinedione which was provided in consideration of the purity of purified 5,5-dimethyl-2,4-oxazolidinedione based on starting urea was 65.5%. | ||
| As the compound represented by the formula (XXIV), there are given for example acid imides corresponding to the compounds represented by the foregoing formula (XXIII) and the compounds described below: ... 2-Thioxo-4-imidazolidinone 2,4-Imidazolidinedione 5,5-Dimethyl-2,4-oxazolidinedione 5,5-Dimethyl-2-thioxo-4-imidazolidinone ... |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 93% | With potassium carbonate; In hexane; water; | 13-1) Production of 5,5-dimethyl-3-(2-nitrobenzyl)oxazolidine-2,4-dione A mixture of <strong>[695-53-4]5,5-dimethyloxazolidine-2,4-dione</strong> (1.9 g, 15 mmol), 2-nitrobenzylchloride (2.6 g, 15 mmol), potassium carbonate (2.5 g, 18 mmol) and N, N-dimethylformamide (15 ml) was heated at 80C for 2 hours while stirring. After cooling, the reaction mixture was mixed with water and extracted with ethyl acetate, and the organic layer was washed with water (twice), then with saturated sodium chloride solution and dried with anhydrous magnesium sulfate. After concentrated under reduced pressure, the organic layer was mixed with hexane, and precipitated solid material was collected by filtration to obtain 5,5-dimethyl-3-(2-nitrobenzyl)oxazolidine-2,4-dione (3.7 g). Yield: 93% Properties: melting point 133.5-134.5C |
[ 695-53-4 ]
[ 695-53-4 ]

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; | To a solution of 7-(3-ethyl-heptyl)-6-(4-formyl-phenoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-2- carbonitrile (720 mg, 1.90 MMOL) in MeOH (30 ml) and THF (30 ml) is added portionwise NaBH4 (100 mg, 2.60 MMOL). The reaction mixture is stirred at rt for 4 h, and the bulk of solvents are removed in vacuo. The residue is diluted with water, and extracted with CH2CI2. The combined organic extracts are washed with brine, and dried over NA2S04, filtered, and concentrated in vacuo. The residue is purified by silica gel column chromatography to give the alcohol 7-(3-ethyl-heptyl)-6-(4-hydroxy-methyl-phenoxymethyl)-7h-pyrrolo[2,3- d]pyrimidine-2-carbonitrile. To a solution of said, alcohol (140 mg, 0.36 MMOL), 5,5-dimethyl-oxazolidinedione (46 mg, 360 MMOL), and Ph3P (105 mg, 0.40 MMOL) in THF (2 mL) is added DEAD (0.25 ml, 0.46 MMOL). The reaction mixture is stirred at rt for overnight. After concentration, the residue is purified by RP-HPLC to give the title compound; Rf 0. 38 (n- Hexane: EtOAc=1: 1) ;H-HMR (400 MHz) 0.92-1. 00 (m, 2H), 1. 18-1. 25 (m, 3H), 1. 30-1. 40 (m, 1H), 1. 58 (s, 6H), 1. 68-1. 78 (m, 7H), 4.35-4. 39 (m, 2H), 4.62 (s, 2H), 5.22 (s, 2H), 6. 71 (s, 1H), 6. 95 (dd, 2H), 7.37 (dd, 2H), 8. 96 (s, 1H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| (step [A]) A 500-milliliter three-necked flask fitted with a stirrer, a reflux condenser and a thermometer was charged with 236.3 g (2.00 mols) of methyl 2-hydroxyisobutyrate, 60.1 g (1.00 mol) of urea and 1.5 g of lead oxide, and the mixture was heat-refluxed at 140C and 700 torr while being stirred. After the reaction was conducted for 3 hours, the temperature of the reaction solution reached 170 C Thereaction solution was cooled to obtain 247.7 g of the reaction solution. The composition of the reaction solution was analyzed through liquid chromatography. Consequently, unreacted methyl 2-hydroxyisobutyrate was 104.3 g, 5,5-dimethyl-2,4-oxazolidinedione formed was 121.9 g, byproduct 2-hydroxyisobutyric acid amide was 11.8 g, and by-product methyl carbamate was 3.1 g. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With potassium carbonate; In ethyl acetate; acetone; | Preparation of 2-[3-(1-adamantyl)-2-(5,5-dimethyl-2,4-dioxooxazolidinyl)-3-oxopropanamido]-4-nitroanisole [5] A suspension of 16.28 g (0.04 mol) of [4], 5.17 g (0.04 mol) of <strong>[695-53-4]5,5-dimethyloxazolidine-2,4-dione</strong>, and 16.58 g (0.12) mol of anhydrous potassium carbonate in 380 mL of dried acetone was refluxed for 3 hours. Thin layer chromatographic analysis indicated that the reaction was complete. The reaction mixture was concentrated in vacuoto yield an orange-colored solid. It was dissolved in ethyl acetate and the organic layer was washed with HCl (10%) and brine until neutrality. The organic layer was dried, filtered, and concentrated to yield an oil which solidified upon standing. It was triturated in ligroin. The final dried product (15.92 g, 79.8%) gave one spot on TLC. All analytical data confirmed the assigned structure. |
[ 695-53-4 ]

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 65% | With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 2h; | To a solution of 150mg (0.488mol) of the compound obtained in the Example 122 in 5mL of tetrahydrofuran were added 75.6mg (0.586mmol) of 5,5-dimethyloxazolidine-dione, 154mg (0.586mmol) of triphenylphsophine and 267muL (0.586mmol) of diethyl azodicarboxylate (40% toluene solution), and the mixture was stirred for 2 hours at room temperature. After the reaction, water was added to the reaction mixture and the mixture was extracted with dichloromethane. The organic layer was dried over with anhydrous sodium sulfate and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: dichloromethane/acetone = 2/1 for first trial, and hexane/ethyl acetate = 2/1 for second trial) to give 133mg (65%) of the title compound. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Example 124(3R*,4R*)-N-[3,5-bis(trifluoromethyl)benzyl]-1-[2-(5,5-dimethyl-2,4-dioxo-1,3-oxazolidin-3-yl)ethyl]-3-(4-fluoro-2-methylphenyl)-N-methylpiperidine-4-carboxamide monohydrochloride(step 1)To a solution of <strong>[695-53-4]5,5-dimethyl-1,3-oxazolidine-2,4-dione</strong> (500 mg) in DMF (10 mL) was added NaH (186 mg) at room temperature, and the mixture was stirred for 5 min. 1-Bromo-2-chloroethane (430 muL) was further added, and the mixture was stirred at room temperature for 4 days. The reaction mixture was concentrated under reduced pressure, and ethyl acetate was added to the residue. The organic layer was washed with aqueous citric acid solution and water and dried, and the solvent was evaporated under reduced pressure to give crude 3-(2-chloroethyl)-<strong>[695-53-4]5,5-dimethyl-1,3-oxazolidine-2,4-dione</strong> as a colorless oil. |