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

HRID 875029Notes

Reaction equation

HRID 875029 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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)+

Workup

  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

Sources & evidence

ORD record
ord-4dbd373b9a984bb6beb36f3c59875b3d
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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