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CAS No. : | 634614-25-8 | MDL No. : | MFCD10687166 |
Formula : | C12H12N2O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 264.23 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
6.16 g | With bromine; sodium hydroxide; In water; at 55℃; for 3h;Cooling with ice; | Under ice-cooling, to a 1M aqueous solution of sodium hydroxide (124 ml) was added dropwise bromine (6.60 ml), and then after adding <strong>[4474-86-6](R)-2-benzyloxycarbonylaminosuccinamic acid</strong> (10.0 g), the mixture was stirred at 55 C. for 3 hours. This reaction solution was cooled to room temperature, washed twice with diethyl ether, and then a 6M aqueous solution of hydrochloric acid (21 ml) was added thereto. This reaction mixture was left to stand at 4 C. for 3 days, and a precipitated solid was collected by filtration to give the titled compound (6.16 g). 1H-NMR (DMSO-D6) delta: 3.19-3.22 (m, 1H), 3.63 (dd, 1H, J=10.2, 5.0 Hz), 4.67 (dd, 1H, J=10.2, 3.3 Hz), 5.14-5.18 (m, 2H), 7.28-7.40 (m, 5H), 7.56 (s, 1H), 13.24 (br s, 1H). |
To a solution of [NAOH] (2.48 g, 61.97 mmole) in water (50 ml) at [0C] is added bromine (3.305 g, 20.66 mmole). After 5 min, (R)-NCbz- Asparagine is added to the above solution and the mixture is stirred at [50C] for lh. Addition of 5% Na2S203 and then extraction with Et20 [(1X100] [ML).] The aqueous phase is acidified to pH 2 with 6N [HC1] and the reaction mixture is left in the fridge for 6 days. Filtration of the crystals, and recrystalization in hot water to afford (4R)-3- [ (benzyloxy) carbonyl] -2-oxoimidazolidine-4-carboxylic acid as a white powder. 1H NMR (DMSO-D6) [delta] 7.5-7.2 (M, 5H), 6.5 (SL, 1H), 5.28 (S, 2H), 4.88 (M, 1H), 3.88 (M, 1H), 3.5 (M, 1H) ; MS 263.2 (M-1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
565 mg | With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; at 20.0℃; under 760.051 Torr; for 24.0h; | Under nitrogen atmosphere, to a solution of (R)-2-oxoimidazolidine-1,5-dicarboxylic acid 1-benzyl ester (1.61 g) in methanol/tetrahydrofuran (4/1, 20 ml) was added 10 wt % palladium on carbon (161 mg) at room temperature, and the mixture was stirred for 24 hours under one atmosphere of hydrogen. Under nitrogen atmosphere, palladium on carbon in this reaction solution was filtered off through Celite, and the filtrate was concentrated under reduced pressure. To the resulting residue were added diisopropyl ether and n-hexane, and the mixture was stirred. A solid was collected from this suspension by filtration, and dried under reduced pressure to give the titled compound (565 mg). |