Carbamimidic acid, methyl ester, sulfate (1:1) → HCID 178498443, 화합물

HRID 1452654노트

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HRID 1452654 반응식
[C:1](/[C:4](=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)/[C:5]([O:7][CH3:8])=[O:6])(=O)[CH3:2].S(O)(O)(=O)=O.[CH3:22][O:23][C:24](=[NH:26])[NH2:25].C([O-])(O)=O.[Na+]>C(O)C>[F:16][C:13]1[CH:14]=[CH:15][C:10]([CH:9]2[NH:26][C:24]([O:23][CH3:22])=[N:25][C:1]([CH3:2])=[C:4]2[C:5]([O:7][CH3:8])=[O:6])=[CH:11][CH:12]=1

참가 물질

5

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HCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)HCID 516892Sodium BicarbonateHCID 10751489methyl (2Z)-2-acetyl-3-(4-fluorophenyl)-2-propenoate

생성물 1

HCID 178498443HCID 178498443, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of methyl (2Z)-2-acetyl-3-(4-fluorophenyl)-2-propenoate (0.220 mole, 48.8 g), O-methyl isourea hydrogensulfate (53.40 g, 0.310 mol, 1.5 eq.), NaHCO3 (61.74 g, 0.74 mole, 3.5 equiv.) and ethanol (1.2 L) was refluxed for 24 h, cooled to room temperature, and filtered. The solid was washed with ethanol (200 mL) and the combined filtrate was concentrated in vacuo. The residue was purified by chromatography (silica gel, hexanes/EtOAc/Et3N 50:50:0.1) to yield a mixture of tautomers (4:1, 33.0 g, 53.9%). 1H NMR (CDCl3) δ 7.32-7.24 (m, 2H), 7.04-6.95 (m, 2H), 5.81 (s, 1H), 5.38 (d, 1H, J=2.9 Hz), 4.00 (s, 3H), 3.63 (s, 3H), 2.34 (s, 3H).

후처리

  1. temperaturewas refluxed for 24 h
  2. filtrationfiltered
  3. washThe solid was washed with ethanol (200 mL)
  4. concentrationthe combined filtrate was concentrated in vacuo
  5. customThe residue was purified by chromatography (silica gel, hexanes/EtOAc/Et3N 50:50:0.1)
  6. customto yield
  7. additiona mixture of tautomers (4:1, 33.0 g, 53.9%)

출처 및 근거

ORD 기록
ord-960bda8449c34f0fade8e1af02e30c9b
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473698B2

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