2-Bromomethyl-4,5-diphenyl-oxazole → HCID 54409140, compound

HRID 2379548Notes

Reaction equation

HRID 2379548 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][CH:16]=1)[O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])(=[O:3])[CH3:2].[Li+].CC([N-]C(C)C)C.Br[CH2:26][C:27]1[O:28][C:29]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:31]=1>C1COCC1.[NH4+].[Cl-].CCOCC>[C:1]([N:4]([CH2:26][C:27]1[O:28][C:29]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:31]=1)[C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][CH:16]=1)[O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 5685992-Bromomethyl-4,5-diphenyl-oxazoleHCID 2724682Lithium diisopropylamideHCID 28829494HCID 28829494, compound

Product 1

HCID 54409140HCID 54409140, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of methyl [3-(acetylamino)phenoxy]acetate (1.00 g, 4.5 mmol) in dry THF (20 mL) was added dropwise to a solution of LDA (0.53 g, 5 mmol) in dry THF (5 mL) maintained at about -78° C. under an atmosphere of N2. The mixture was warmed to about 0° C. and stirred about 5 minutes, cooled to about -78° C. and a solution of 2-bromomethyl-4,5-diphenyloxazole (1.41 g, 4.5 mmol) in THF (10 mL) added dropwise. The solution was allowed to warm to room temperature, stirred for about 18 hours and diluted with a mixture of saturated NH4Cl solution and Et2O. The organic phase was 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 EtOAc and hexanes (13:7) as eluent to give methyl [3 -[N-acetyl-[(4,5-diphenyl-2-oxazolyl)methyl]amino]phenoxy]acetate (0.85 g, 42%). IR (Film) 1750 (CO2CH3), 1670 (NCOCH3) cm-1 ; 1H NMR (CDCl3) δ1.92 (3H, s, COCH3), 3.70 (3H, s, CO2CH3), 4.55 (2H, s, OCH2), 5.10 (2H, s, NCH2) 6.75-6.95 (3H, m, aromatic H), 7.20-7.40 (7H, m, aromatic H), 7.45-7.60 (4H, m, aromatic H); MS m/z 457 (MH+).

Workup

  1. temperatureThe mixture was warmed to about 0° C.
  2. temperaturecooled to about -78° C.
  3. temperatureto warm to room temperature
  4. stirringstirred for about 18 hours
  5. customThe organic phase was separated
  6. washwashed with H2O and saturated NaCl solution
  7. dry with materialdried over MgSO4
  8. customThe solvent was evaporated
  9. customthe residue chromatographed on a column of silica gel using
  10. additiona mixture of EtOAc and hexanes (13:7) as eluent

Sources & evidence

ORD record
ord-19eb3cfc27d642888286b216b6d6c759
Source dataset
uspto-grants-1994_11
Patent number
US05362879

Reaction notes

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