Potassium Hydroxide → 2-[(Tert-butoxycarbonyl-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-amino)-methyl]-benzoic acid ethyl ester

HRID 352442Notes

Reaction equation

HRID 352442 reaction equation
[OH-].[K+].[C:3]([O:7][C:8](=[O:31])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:12][CH:11]=1)([CH3:6])([CH3:5])[CH3:4].[CH2:32]([O:34][C:35](=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[CH2:42]Br)[CH3:33]>CS(C)=O>[CH2:32]([O:34][C:35](=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[CH2:42][N:9]([C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:31])[C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:14][CH:15]=1)[CH3:33]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 11032082Ethyl 2-(bromomethyl)benzoateHCID 69486797{4-[2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-carbamic acid tert-butyl ester

Product 1

HCID 694866072-[(Tert-butoxycarbonyl-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-amino)-methyl]-benzoic acid ethyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a suspension of 3.41 g of powdered KOH in 110 ml of DMSO was added at 22° C. 6.00 g of {4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-carbamic acid tert-butyl ester and the suspension was stirred for 25 min. A solution of 7.40 g of 2-bromomethyl-benzoic acid ethyl ester in 10 ml of DMSO was added slowly keeping the temperature at 15-20° C. and stirring was continued at 22° C. for 2.5 h. The dark mixture was partitioned between 500 ml of a saturated aqueous NH4Cl and 200 ml of AcOEt, the organic layer was washed with saturated aqueous NH4Cl and water, dried and evaporated. The residue was purified by chromatography (SiO2, n-hexane/AcOEt 4:1) to give 7.96 g of the title compound as a pale yellow oil. MS: (M+H)+ 557.3.

Workup

  1. additionwas added at 22° C
  2. customat 15-20° C.
  3. customThe dark mixture was partitioned between 500 ml of a saturated aqueous NH4Cl and 200 ml of AcOEt
  4. washthe organic layer was washed with saturated aqueous NH4Cl and water
  5. customdried
  6. customevaporated
  7. customThe residue was purified by chromatography (SiO2, n-hexane/AcOEt 4:1)

Sources & evidence

ORD record
ord-916188e7e8ba4087be5d272a3211af8f
Source dataset
uspto-grants-2004_06
Patent number
US06747049B2

Reaction notes

Loading…