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

HRID 875029노트

반응식

HRID 875029 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)+

후처리

  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

출처 및 근거

ORD 기록
ord-4dbd373b9a984bb6beb36f3c59875b3d
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08981084B2

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