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CAS No. : | 69651-48-5 | MDL No. : | MFCD01860630 |
Formula : | C13H17NO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LRWJRIFKJPPAPM-JTQLQIEISA-N |
M.W : | 267.28 | Pubchem ID : | 11300124 |
Synonyms : |
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Chemical Name : | (S)-2-((tert-Butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetic acid |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319 | 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 |
---|---|---|
66% | In methanol; hexane; benzene; at 0℃; | In a 50 mL round bottomed flask was added a 1:1 mixture of benzene:methanol and N-tert-butoxycarbonyl-(S)-4-hydroxyphenylglycine (2.8 g, 11 mmol). The solution was cooled to 0 C. and a 2 M solution of trimethylsilyldiazomethane (Aldrich Chemical Co.) in hexane was added with vigorous stirring until a slight yellow color persisted. Then the reaction mixture solvents were removed under reduced pressure and the crude product was purified by flash chromatography (80/20 hexane/ethyl acetate) to give N-tert-butyloxycarbonyl-(S)-4-hydroxyphenylglycine, methyl ester (2.05 g, 7.3 mmol) (66% yield). 300 MHz 1H NMR (CDCl3): delta1.43 (s, 9H), 3.71 (s, 3H), 5.22 (br d, 1H), 5.57 (1H, br d), 5.80 (br s, 1H), (6.7 (d, 2H, J=8 Hz), 7.17 (d, 2H, J=8 Hz). |
With methanol; In toluene; | Preparation 15: (.S)-ferf-Butoxycarbonylamino-(4-hydroxyphenyl)acetic acid methyl ester; Trimethylsilyldiazomethane (5.40 mL, 7.62 mmol) was added dropwise to a solution of (5)-ferf-butoxycarbonylamino-(4-hydroxyphenyl)acetic acid (Preparation 14, 2.00 g, 7.48 mmol) in toluene:MeOH (4:1, 50 mL). The clear solution turned yellow and the MeOH was removed in vacuo. The remainder was diluted with EtOAc (100 mL), washed with H2O (50 mL), saturated NaHCO3 solution (50 mL) and brine (50 mL) before being dried (MgSO4), filtered and concentrated in vacuo, azeotroping several times with Et2O, to afford the title compound: RT = 2.98 min, m/z (ES+) = 282.1 [M + H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | STEP 2: To a solution of (S)-2-(tert-butoxycarbonylamino)-2-(4- hydroxyphenyl)acetic acid (1.60 g, 5.98 mmol) in dimethylformamide (20 mL) was added potassium carbonate (1.85 g, 13.42 mmol), and the mixture was stirred at room temperature for thirty minutes, followed by the addition of methyl iodide (0.76 mL, 12.20 mmol). The reaction mixture was then stirred at room temperature for 18 hours. The solvent was evaporated and the residue was partitioned between ethyl acetate (250 mL) and water (50 mL). The organic layer was separated and washed with saturated aqueous sodium hydrogencarbonate, water and brine, dried over sodium sulfate, filtered and the solvent was concentrated to give (S)-methyl 2-(tert- butoxycarbonylamino)-2-(4-methoxyphenyl)acetate (1.8 g, quantitative). 1H NMR (400 MHz, CDCl3): 7.16 (d, 2H), 6.72 (d, 2H), 5.68 (d, IH), 5.14 (d, IH), 3.62 (s, 3H), 3.56 (s, 3H), 1.24 (s, 9H). MS (EI) for C15H21NO5: 294 (MH"). | |
99% | With potassium carbonate; In N,N-dimethyl-formamide; at 25℃; for 18h; | The solution was stirred at 25 C. for 18 hours and then diluted with ethyl acetate and washed with 5% H3PO4 aqueous solution and saturated aqueous sodium bicarbonate solution. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound as a light colored solid. The crude material was taken on directly to the next step. (1.06 g, 99% yield) MS (ESI+) m/z=318 (M+Na)+ |