Diisopropylethylamine → Methyl 2-(4-fluorophenyl)-4,5-dihydrooxazole-4-carboxylate

HRID 875029ノート

反応式

HRID 875029 の反応式
C(N(CC)C(C)C)(C)C.Cl.[F:11][C:12]1[CH:21]=[CH:20][C:15]([C:16](=[NH:19])[O:17][CH3:18])=[CH:14][CH:13]=1.Cl.[CH3:23][O:24][C:25](=[O:30])[CH:26](CO)N>C(Cl)Cl>[F:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]2[O:17][CH2:18][CH:26]([C:25]([O:24][CH3:23])=[O:30])[N:19]=2)=[CH:20][CH:21]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 517373Methyl DL-serinate hydrochlorideHCID 14685563Methyl 4-fluorobenzimidate hydrochloride

生成物 1

HCID 22184737Methyl 2-(4-fluorophenyl)-4,5-dihydrooxazole-4-carboxylate収率 81%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

N,N-diisopropylethylamine (11 mL, 63.3 mmol) was added dropwise to a solution of methyl 4-fluorobenzimidate hydrochloride (10 g, 52.74 mmol) and DL-serine methyl ester HCl salt (9.9 g, 63.63 mmol) in dry CH2Cl2 (200 mL) at 0° C. The reaction mixture was stirred at room temperature for 24 h and then concentrated under reduced pressure. The reaction mixture was diluted with CH2Cl2 and the organic layer was washed with H2O and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to get methyl 2-(4-fluorophenyl)-4,5-dihydrooxazole-4-carboxylate (9.5 g, yield 81%) as an orange liquid. 1H NMR (300 MHz, CDCl3) δ 8.02-7.97 (m, 2H), 7.13-7.07 (t, J=8.7 Hz, 2H), 4.98-4.92 (m, 1H), 4.73-4.57 (m, 2H), 3.83 (s, 3H). MS (ESI) m/z: Calculated for C11H10FNO3: 223.06. found: 223.8 (M+H)+

後処理

  1. concentrationconcentrated under reduced pressure
  2. additionThe reaction mixture was diluted with CH2Cl2
  3. washthe organic layer was washed with H2O and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-4dbd373b9a984bb6beb36f3c59875b3d
出典データセット
uspto-grants-2015_03
特許番号
US08981084B2

反応ノート

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