Structure of Fmoc-N-Me-Ile-OH
CAS No.: 138775-22-1
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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.
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| CAS No. : | 138775-22-1 |
| Formula : | C22H25NO4 |
| M.W : | 367.44 |
| SMILES Code : | [H][C@@]([C@@H](C)CC)(N(C)C(=O)OCC1C2=CC=CC=C2C2=C1C=CC=C2)C(O)=O |
| MDL No. : | MFCD00153389 |
| InChI Key : | IQIOLCJHRZWOLS-XOBRGWDASA-N |
| Pubchem ID : | 15433034 |
| 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.

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| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 89% | With potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; | To a solution of Fmoc-NMe-Ile (8.0 g, 21.8 mmol) in anhydrous DMF(156 mL) was added benzyl bromide (5.2 mL, 43.6 mmol) andpotassium bicarbonate (6.5 g, 66.3 mmol). The reaction was astirred overnight at room temperature, and then diluted with ethylacetate (150 mL).The whole mixture was successively washedwith water (100mL), saturated NaHCO3 (100 mL), and brine (100 mL). The organiclayer was dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography (petroleum ether/ethyl acetate, 10:1 to 5:1) to yield8 (8.9 g, 89%) as a colorless oil. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 4.9 g | With triethylsilane; trifluoroacetic acid; In chloroform; at 20℃; for 10h;Inert atmosphere; | To the above crude oxazolidinone in CHC13 (67 mL) was added trifluoroacetic acid(67 mL) and triethylsilane (6.7 mL, 42.3mmol). The solution was stirred at roomtemperature for 10 h followed by concentration in vacuo, affording an oil residue. Theoil was re-dissolved in CH2C12 and re-concentrated for three times. The resultant oilwas crystallized when standing. The crystals were collected and dissolved in ether andre-concentrated. The obtained white solid was washed with 5% ether in hexane anddried, yielding a pure white solid (4.9 g, 94%). |
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