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CAS No. : | 83079-77-0 | MDL No. : | MFCD06410793 |
Formula : | C14H21NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CANQRTXTMVVNCH-LBPRGKRZSA-N |
M.W : | 235.32 | Pubchem ID : | 14523456 |
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 |
---|---|---|
With sulfuric acid; In 1,4-dioxane; at -78 - 20℃; for 72h; | The solution of starting material is then cooled to -78 C. and the cold liquid isobutylene is added. The mixture is stirred at room temp in a pressure bottle for 3 days. The bottle is then cooled to -78 C. and opened. It is then stirred while open and allowed to warm up in an ice bath. After 20 minutes of stirring, 55 ml of 2N NaOH are added slowly at 0 C. The product is extracted with ether and washed with dilute sodium bicarbonate. The solution is dried over sodium sulfate and the solvent is removed to give 4.9 g of the t-butyl ester as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; | To 100 ml of methylene chloride are added 2.50 g of 2c. This dissolves to give a clear orange solution after 2.66 ml of triethylamine are added. While stirring, 2.33 g of the amino t-butyl ester are added. This is followed by the addition of 3.33 g of HOBt and 3.86 g of EDC in that order. The solution is stirred over two nights. The solution is then washed with 10% citric acid, water, sodium bicarbonate, and brine. The organic layer is dried over sodium sulfate and the solvent removed to afford 3.90 g of the coupled intermediate as an orange foam. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With triethylamine; In dichloromethane; at 20℃; for 0.5h; | To a solution of 11i (0.0509 g, 0.22 mmol) in CH2Cl2 (1.5 mL) were added Et3N (0.0404 g, 0.40 mmol) and PhCOCl (0.0464 g, 0.33 mmol) successively. The reaction mixture was stirred at rt for 30 min and purified by flash chromatography (silica gel, petroleum ether/EtOAc=10/1 to 5/1) to afford N-benzoyl amino ester 12i (0.0622 g, 83%) as white solid. The sample was subjected to chiral HPLC (chiralcel OD-H column) to determine the enantiomeric excess. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A well-dried Schlenk tube charged with molecular sieves 4 ? (0.030 g), α-keto ester 8i (0.0702 g, 0.30 mmol), o-OHC6H4CH2NH2 (0.0739 g, 0.60 mmol), and catalyst 7 (0.0110 g, 0.030 mmol) was evacuated and refilled with N2. The process was repeated three times. Dry benzene (3.0 mL) was added. Upon stirring at 25 C for 48 h, the reaction mixture was concentrated. The resulting residue was treated with THF (3.0 mL), followed by the addition of aqueous 1 N HCl (3.0 mL). Upon stirring at rt for 5 h, the mixture was diluted with water (10 mL) then washed with hexane (3×10 mL). The organic phase was extracted with aqueous 1 N HCl. The aqueous phases were combined, brought to pH 8.0 with solid NaHCO3, extracted with CH2Cl2 (5×10 mL), and the organic extracts were dried (MgSO4), filtered, concentrated, and purified by flash chromatography (silica gel, petroleum ether/EtOAc=5/1 then EtOAc/CH3OH=10/1) to give α-amino ester 11i (0.0607 g, 86% yield); +13.1 (c 0.89, CHCl3) (57% ee). |