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Chemical Structure| 89531-66-8 Chemical Structure| 89531-66-8

Structure of 89531-66-8

Chemical Structure| 89531-66-8

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Product Details of [ 89531-66-8 ]

CAS No. :89531-66-8
Formula : C6H11NO3
M.W : 145.16
SMILES Code : O=C(OCC)CN(C)C=O
MDL No. :MFCD21121745

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Application In Synthesis of [ 89531-66-8 ]

* 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.

  • Upstream synthesis route of [ 89531-66-8 ]

[ 89531-66-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 89531-66-8 ]
  • [ 177760-04-2 ]
YieldReaction ConditionsOperation in experiment
61%
Stage #1: With sodium hydride; formic acid ethyl ester; sodium nitrite In tetrahydrofuran; cyclohexane; mineral oil at 20℃; for 3.5 h;
Stage #2: With hydrogenchloride In ethanol; water at 110℃; for 2 h;
Stage #3: With CYANAMID; sodium hydroxide In ethanol; water for 1.5 h; Reflux
To a solution of N-formyl sarcosine ethyl ester (3) (29.6 g,204 mmol) in an equal mixture of ethyl formate and THF (190 mL)with cyclohexane (12 mL), was added slowly NaH (60percent wt inmineral oil, 12.5 g, 313 mmol) at room temperature. After the addition was completed and hydrogen release stopped, the reaction mixture was allowed to stirred during 3.5 h. The reaction mixture was concentrated under vacuum. The obtained solid was suspended in a solution of EtOH (250 mL) containing concentrated aq.HCl 32percent (61 mL) and refluxed for 2 h. The hot reaction mixture was filtered and the resulting colourless solid was washed with boilingEtOH (2 150 mL). The filtrate was concentrated under vacuum and diluted with a mixture of EtOH/water (500 mL, 70/30, v/v). The pH of the solution was adjusted to 3, using an aqueous 5M solution of NaOH and cyanamide (17.5 g, 416 mmol) was added. The resulting mixture was refluxed for 1.5 h, then cooled to rt and concentrated under reduced pressure to approximately 1/8 of the initial volume. The pH of the remaining solution was adjusted to 9-10 with a saturated aqueous solution of potassium carbonate, after cooling in an ice-water bath. The precipitate formed was removed by filtration, washed with water (2 10 mL) and dried under vacuum at 40 °C overnight to afford compound 4 (16.9 g,99.9 mmol) as a pale yellow to orange solid. A supplementary fraction can be yielded after extraction of the remaining filtrate with ethyl acetate (3 100 mL). The combined organic layers weredried over MgSO4, filtered and evaporated under reduced pressure.The residue was purified by column chromatography on silica gelusing ethyl acetate/ethanol (95/5, v/v with 1percent NH4OH) as eluent to yield compound 4 (3.78 g, 22.3 mmol). Yield 61percent; Rf 0.33 (SiO2,EtOAc/EtOH, 9/1, v/v); mp 131 C (Lit [40]. mp 130-133 °C); IR(ATR) n cm1 3390, 3119, 1647, 1542, 1168, 750, 737; 1H NMR(CDCl3, 400 MHz) δ 7.39 (s, 1H, CHAr), 4.66 (br.s, 2H, NH2), 4.25 (q,2H, 3J 7.1 Hz, CH2CH3), 3.65 (s, 3H, NCH3), 1.32 (t, 3H, 3J 7.1 Hz,CH2CH3); 13C NMR (DMSO‑d6, 126 MHz) δ 159.68 (CO), 154.27(CArNH2), 136.02 (CHAr), 116.88 (CArCO), 58.82 (OCH2), 30.17 (NCH3),14.30 (CH2CH3).
References: [1] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 51 - 67.
 

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