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CAS No. : | 109183-71-3 | MDL No. : | MFCD00133638 |
Formula : | C13H23NO4 | Boiling Point : | - |
Linear Structure Formula : | C4H9CO2NHCHCO2HC6H11 | InChI Key : | QSUXZIPXYDQFCX-JTQLQIEISA-N |
M.W : | 257.33 | Pubchem ID : | 7004938 |
Synonyms : |
(S)-2-((tert-Butoxycarbonyl)amino)-2-cyclohexylacetic acid
|
Chemical Name : | (S)-2-((tert-Butoxycarbonyl)amino)-2-cyclohexylacetic acid |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 4-methyl-morpholine; sodium tetrahydroborate; isobutyl chloroformate; | N-(tert-Butoxycarbamoyl)-(1S)-1-cyclohexyl-2-hydroxyethylbutylamine was prepared from N-(tert-Butoxycarbamoyl)-(L)-cyclohexylglycine according to Method B1a, Step 2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; | Example 1 Step 1 (2S)-N-CYCLOBUTYL-N-METHYL-2- (TERT-BUTOXYCARBONYLAMINO)-2- cyclohexylacetamide N-Methylcyclobutylamine hydrochloride (159 mg) synthesized by the method described in Journal of Medicinal Chemistry, 1994, 37,3482 was dissolved in N, N-DIMETHYLFORMAMIDE (4 ml), and L- tert-butoxycarbonylcyclohexylglycine hydrate (159 mg), (benzotriazole-1-yloxy) tripyrrolidinophosphonium hexafluorophosphate (676 mg) and diisopropylethylamine (0.453 ml) were added. The mixture was stirred overnight at room temperature. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution, 5% aqueous potassium hydrogen sulfate solution and saturated brine, and dried over sodium sulfate. The drying agent was filtered off and the filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (hexane : ethyl acetate=3: 1) to give the title compound. 1H-NMR (8PPM, CDC13) 1.13-1. 37 (5H, m), 1.42 (9H, s), 1.59-1. 71 (9H, m), 2.10-2. 29 (4H, m), 4.39-4. 55 (lH, m), 4.80-4. 90 (0. 4H, m), 5.25- 5.33 (0.6H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | General procedure:A 200 mL roundbottom flask was charged with (S)-2-(tertbutoxycarbonylamino)- 2-cyclohexylacetic acid (2.56 g, 9.95 mmol) and HOBt hydrate (1.70 g, 11.10 mmol). Anhydrous DMF (15.0 mL) was added, and the solution was cooled to 0 C. 4-Methylmorpholine (1.10 mL, 10.0 mmol) was added, followed by EDCI (2.01 g, 10.49 mmol). Additional DMF (3.0 mL) was added, and the mixture was allowed to stir at 0 C for 15 minutes. Meanwhile, a separate 250 mL roundbottom flask containing crude <strong>[550378-39-7](S)-benzyl 3-aminopyrrolidine-1-carboxylate hydrochloride</strong> (Intermediate 5; 10.1 mmol) was treated with anhydrous DMF (7.0 mL) and 4-methylmorpholine (1.20 mL, 10.9 mmol), and the resulting solution was cooled to 0 C. The mixture of the activated ester was then added via pipette, using additional DMF (2 x 2.5 mL) to fully transfer the reagent. The reaction was then allowed to stir at 0 C with slow warming to room temperature. After stirring overnight, the reaction was partitioned between EtOAc and 1 N HCl. The aqueous layer was extracted with EtOAc, and the combined organics were washed with saturated NaHCO3, water, and then brine, and were dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography (Rf in 50:50 hexanes:EtOAc = 0.29) to give the product as a colorless foam (3.42 g, 75%). |