Sodium hydride → HCID 9935116, compound

HRID 2379552Notes

Reaction equation

HRID 2379552 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=1)[O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:5])[CH3:2].[H-].[Na+].Br[CH2:22][C:23]1[O:24][C:25]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:27]=1>CN(C=O)C.O>[C:28]1([C:26]2[N:27]=[C:23]([CH2:22][N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:7]3[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=3)[O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[O:24][C:25]=2[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 5685992-Bromomethyl-4,5-diphenyl-oxazoleHCID 54500376HCID 54500376, compound

Product 1

HCID 9935116HCID 9935116, compoundYield 19.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of methyl [3-[(ethoxycarbonyl) amino]phenoxy]acetate (4.10 g, 16 mmol) was dissolved in DMF (40 mL), NaH (0.94 g of a 50% dispersion in mineral oil, 19 mmol) added and the mixture stirred at room temperature for about 20 minutes. 2 -Bromomethyl-4,5-diphenyl-oxazole (5.10 g, 16 mmol) in DMF (15 mL) was added dropwise and the mixture stirred at room temperature for about 3 hours. The mixture was diluted with H2O, extracted with Et2O and the combined extracts washed with H2O. After drying over MgSO4, the solvent was evaporated and the residue chromatographed twice on a column of silica gel using hexane/EtOAc (4:1) for the first column and CH2Cl2 /MeOH (24:1) for the second to give methyl [3-[[(4,5-diphenyl-2-oxazolyl)methyl](ethoxycarbonyl)amino]phenoxy]acetate (1.50 g, 19%). IR (film) 1765, 1710 cm-1 ; 1H NMR (CDCl3) δ1.22 (3H, t, J=8 Hz, OCH2CH3), 3.75 (3H, s, CO2CH3), 4.21 (2H, q, J=8 Hz, OCH2CH3), 4.47 (2H, s, OCH2CO2CH3), 5.00 (2H, s, CH2 -oxazole), 5.28 (0.2H, s, CH2Cl2), 6.79 (1H, dd, J=9 Hz, J'=2 Hz, aromatic H), 7.05 (2H, m, aromatic H), 7.20 to 7.40 (7H, m, aromatic H) , 7.50 to 7.70 (4H, m, aromatic H); MS m/z 487 (MH+).

Workup

  1. stirringthe mixture stirred at room temperature for about 3 hours
  2. extractionextracted with Et2O
  3. washthe combined extracts washed with H2O
  4. dry with materialAfter drying over MgSO4
  5. customthe solvent was evaporated
  6. customthe residue chromatographed twice on a column of silica gel

Sources & evidence

ORD record
ord-41f2a42c530341c4b93737a4b3aa450e
Source dataset
uspto-grants-1994_11
Patent number
US05362879

Reaction notes

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