2-Bromomethyl-4,5-diphenyl-oxazole → HCID 54321190, compound

HRID 2379550Notes

Reaction equation

HRID 2379550 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:7]=[C:8]([CH:15]=[CH:16][CH:17]=1)[O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[O:4].Br[CH2:19][C:20]1[O:21][C:22]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:24]=1>C1COCC1.[NH4+].[Cl-].CCOCC>[C:25]1([C:23]2[N:24]=[C:20]([CH2:19][N:5]([C:3]([O:2][CH3:1])=[O:4])[C:6]3[CH:7]=[C:8]([CH:15]=[CH:16][CH:17]=3)[O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[O:21][C:22]=2[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 2

HCID 5685992-Bromomethyl-4,5-diphenyl-oxazoleHCID 53967812HCID 53967812, compound

Product 1

HCID 54321190HCID 54321190, compoundYield 50.1%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

NaH (0.34 g of a 50% dispersion in mineral oil, 3.5 mmol) was washed twice with hexanes and covered with dry THF (10 mL). A solution of methyl [3-[(methoxycarbonyl)amino]phenoxy]acetate (0.75 g, 3 mmol) in dry THF (10 mL) was added and the mixture stirred at room temperature. After about 30 minutes, a solution of 2-bromomethyl-4,5-diphenyl-oxazole (0.99 g, 3 mmol) in THF (7 mL) was added and the mixture stirred overnight at room temperature. The mixture was diluted with saturated NH4Cl solution and Et2O, the organic phase separated, washed with H2O and saturated NaCl solution and dried over MgSO4. The solvent was evaporated and the residue chromatographed on a column of silica gel using a mixture of hexanes and EtOAc (4:1) as eluent to give methyl [3-[[(4,5-diphenyl-2-oxazolyl)methyl](methoxycarbonyl) amino]phenoxy]acetate (0.71 g, 48%). IR (film) 1760, (CO2CH3), 1715 (NCO2CH3) cm-1 ; 1H NMR (CDCl3) δ3.73 (6H, s, CO2CH3), 4.58 (2H, s, OCH2CO2CH3), 4.99 (2H, s, CH2 -oxazole), 6.79 (1H, dd, J=9 Hz, J'=2 Hz, aromatic H), 7.02 (2H, m, aromatic H), 7.20 to 7.45 (7H, m, aromatic H), 7.50 to 7.65 (4H, m, aromatic H); MS m/z 473 (MH+).

Workup

  1. washNaH (0.34 g of a 50% dispersion in mineral oil, 3.5 mmol) was washed twice with hexanes
  2. stirringthe mixture stirred overnight at room temperature
  3. customthe organic phase separated
  4. washwashed with H2O and saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated
  7. customthe residue chromatographed on a column of silica gel using
  8. additiona mixture of hexanes and EtOAc (4:1) as eluent

Sources & evidence

ORD record
ord-73d320d5c9b948d9b219bf5d3a70f1c3
Source dataset
uspto-grants-1994_11
Patent number
US05362879

Reaction notes

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