Carbamimidic acid, methyl ester, sulfate (1:1) → HCID 178498443、化合物

HRID 1452654ノート

反応式

HRID 1452654 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 178498443HCID 178498443、化合物

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-960bda8449c34f0fade8e1af02e30c9b
出典データセット
uspto-grants-2009_01
特許番号
US07473698B2

反応ノート

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