Structure of 87276-51-5
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CAS No. : | 87276-51-5 |
Formula : | C15H18N2O5 |
M.W : | 306.31 |
SMILES Code : | O=C(OC(C)(C)C)NCCON(C(C1=C2C=CC=C1)=O)C2=O |
InChI Key : | UDICTKJZWXXLJB-UHFFFAOYSA-N |
Pubchem ID : | 18929164 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
* 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 |
---|---|---|
100% | In dichloromethane; at 20℃; for 72h; | Step B: [2-(1,3-dioxo-1,3-dihydroisoindol-2-yloxy)-ethyl]-carbamic acid tert-butyl ester (0.842 g, 2.749 mmol) was dissolved in 20 ml of CH2Cl2 and methylhydrazine (150 μL, 2.776 mmol) was added at room temperature. As soon as methylhydrazine was added, a white precipitate was formed. The reaction was stirred at room temperature for 72 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to provide 0.496 g of a viscous oil (102% yield). The crude material was used without further purification |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With hydrazine hydrate; In ethanol; at 20℃; for 2h; | To a solution of N-(2-tert-Boc-aminoethoxy)phthalimide (27a) (3.8 g, 12.4 mmol) in EtOH (38 mL) at room temperature was added hydrazine monohydrate (0.63 mL, 13.0 mmol). The reaction was stirred at room temperature for 2 h. The mixture was filtered and washed with ethyl acetate. The filtrate was concentrated and a white solid was formed. The white solid was removed by filtration and washed with ethyl acetate. This process was repeated three additional times. The combined filtrate was then concentrated to give the product (27b) as a yellow paste (2.16 g, yield 99%). 1H NMR (300 MHz, CDCl3): δ 5.46 (br s, 2H), 4.91 (br s, 1H), 3.70 (m, 2H), 3.35 (m, 2H), 1.44 (s, 9H). |
80% | With hydrazine; In ethanol; at 20℃; for 2h; | General procedure: To a solution of 4a (or 4b-e, 5.8 mmol ) in EtOH (10 mL), was added hydrazine (187 uL, 5.97 mmol)in drop. The reaction mixture was stirred at rt. until the reaction was completed as judged by TLC. Themixture was filtered and the filtrate was concentrated and purified by column chromatography to givethe product 5a-e. 5a was obtained as a white solid (817 mg, 80%). |
78% | With hydrazine hydrate; In ethanol; | The obtained compound 3 (1.78 g, 5.8 mmol) was dissolved in 10 mL of ethanol,Then hydrazine hydrate (187L, 5.97mmoL) was slowly added dropwise to the reaction system,White precipitate appeared in the system,The reaction was monitored by TLC until the substrate was consumed,filter,The filtrate was concentrated,Pass through the column to afford pure Compound 4 (800 mg, 78%). |
55% | With hydrazine hydrate; at 20℃; | Hydrazine monohydrate (0.146 mL, 4.71 mmol, 1.03 eq.) at room temperatureAdd to a solution of compound MC-116-1 (1.4 g, 4.57 mol, 1.0 eq.) in ethanol (10 mL).The reaction was then allowed to react overnight at room temperature. Point plate detection reaction, after the reaction is over,The reaction solution was filtered, and the residue obtained by concentration of filtrate was chromatographed on silica gel.(ethyl acetate / petroleum ether = 1/2) purified to give a colorless oily compoundMC-116-2 (448 mg, 55%). |
255 mg (71%) | Step C: Preparation of (2-aminooxy-ethyl)-carbamic acid tert-butyl ester. The synthesis of the title compound was carried out according to Step D of Example 41 (i) using [2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-ethyl]-carbamic acid tert-butyl ester as the starting material to provide 255 mg (71%) of the desired compound as a yellow liquid. 1H NMR (400 MHz, CDCl3) δ 5.50 (br s, 2H), 5.02 (br s, 1H), 3.71 (t, 2H), 3.36 (q, 2H), 1.45 (s, 9H). | |
With methylhydrazine; In dichloromethane; at 20℃; for 16h; | INTERMEDIATE 37[2-(Aminooxy)ethyl"|carbamic acid tert-butyl ester; Intermediate 36 (1 g, 3.3 mmol) in DCM (20 mL) was treated with methyl- hydrazine (15 8 mg, 3.4 mmol) and the reaction mixture stirred at r.t. for 16 h. The solvent was removed, and the residue was suspended in diethyl ether, filtered and concentrated, to give the title compound. δH (DMSOd6) 6.74-6.65 (IH, br m), 5.99-5.88 (2H, br s), 3.47 (2H, t, J 5.8 Hz), 3.09 (2H, q, J5.8 Hz), 1.38 (9H, s). LCMS (ES") RT 1.93 minutes, 175 (M-H)'. | |
With methylamine; In methanol; dichloromethane; for 2h; | Reference Example 9 tert-Butyl 2-(aminooxy)ethylcarbamate [0251] To a solution of tert-butyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate (1.83 g, 6.00 mmol) described in Reference Example 7 in methylene chloride (11 mL) was gradually added 9.8M methylamine methanol solution (1.83 mL), followed by stirring for 2 hours. The reaction solution was filtered and the filtrate was distilled off under reduced pressure, followed by extracting with 0.5M hydrochloric acid (24 mL). To the resulting aqueous layer were added methylene chloride and 1M sodium hydroxide (18 mL), thereby the target was extracted with ethylene chloride. The resulting organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. 1.038 g of the title compound was afforded as the crude product (yield 98%). 1H NMR (400 MHz, CDCl3) δ 1.45 (m, 9H), 3.35-3.36 (m, 2H), 3.70-3.72 (m, 2H), 4.91 (br s, 1H), 5.47 (br s, 2H); MS m/z 177 [M+H]+. | |
28 g | With hydrazine hydrate; In dichloromethane; at 0℃; for 2.75h; | To a stirred solution of N-Boc-2-(2-aminoethoxy)isoindoline-1 ,3-dione (IX, 97 g, 0.3167 mol) in dichloromethane (970 ml) was added hydrazine hydrate (31.7 g, 0.6334 mol) , at 0C, drop wise, over a period of 45 minutes and the stifling continued further. After 2 hours, the reaction mass was filtered under suction. Filtrate was washed with water (485 ml), and the organic layer was diluted with an aq. solution of 10% potassium hydrogen sulfate (485 ml) and stined for 15 minutes. The aqueous layer was separated, neutralized with solid sodium hydrogen carbonate and extracted with dichloromethane (2 x 485 ml). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain colorless oil, this was used as such for further reaction immediately (28g, overall yield of step II and step III was 60%)Analysis:Mass: 177.2 (M+1) for Molecular Weight of 176.2 and Molecular Formula of C7H16N203. |
With hydrazine; In ethanol; | C. Preparation of 2-(Aminoxy)-1-t-Boc-aminoethane Hydrazine (98%, 2.1 g, 0.065 mol) was added to a solution of crude N-(2-t-Boc-aminoethoxy)phthalimide (20 g, 0.065 mol) in ethanol (50 mL) and the mixture was refluxed for 2 hrs. The solid which formed was removed by filtration and the filtrate was evaporated on a rotary evaporator. The residue thus obtained was triturated with ethyl acetate and the resultant precipitate was removed by filtration. The ethyl acetate solution was evaporated on a rotary evaporator to give the title product amine as an oil. Yield: 10 g. (83%). 1 H NMR (CDCl3) δ 1.48 [s, 9H, C(CH3)3 ], 3.42 (m, 2H, OCH2 CH2 NHtBoc), 4.21 (m, 2H, OCH2 CH2 NHtBoc), 5.68 (bs, 1H, NH), 7.7-7.82 (m, 4H, ArH). | |
With hydrazine hydrate; In ethanol; at 65℃; for 3h; | Tert-butyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate (1.53 g, 5.000 mmol) prepared in step 1, hydrazine hydrate (2.5 g, 50.00 mmol) was dissolved in ethanol (30 ml) and then heated to 65C. Reaction 3h. After the reaction, the filtrate was concentrated, and the filtrate was concentrated and purified by column chromatography to obtain the title compound. |
Tags: 87276-51-5 synthesis path| 87276-51-5 SDS| 87276-51-5 COA| 87276-51-5 purity| 87276-51-5 application| 87276-51-5 NMR| 87276-51-5 COA| 87276-51-5 structure
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