p-Toluenesulfonic acid → Methyl 2-(4-fluorophenyl)benzoxazole-4-carboxylate

HRID 401638Notes

Reaction equation

HRID 401638 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][C:9]2[C:18]([OH:19])=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=O)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1(C)C(C)=CC=CC=1>[F:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]2[O:19][C:18]3[C:9](=[C:10]([C:11]([O:13][CH3:14])=[O:12])[CH:15]=[CH:16][CH:17]=3)[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 59625786Methyl 2-(4-fluoro-benzoylamino)-3-hydroxy-benzoate

Product 1

HCID 59626027Methyl 2-(4-fluorophenyl)benzoxazole-4-carboxylateYield 55%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Methyl 2-(4-fluoro-benzoylamino)-3-hydroxy-benzoate 9dd (7.4 mmol, 1.2 g crude) and 1.3 g (7.5 mmol) of p-toluenesulfonic acid was refluxed in 10 mL of xylene overnight. After cooling saturated NaHCO3 was added and the resulting mixture was extracted with EtOAc. The organic solvent was evaporated to give 1.1 g (55%) of methyl 2-(4-fluorophenyl)benzo[d]oxazole-4-carboxylate, 9ee. MS m/z (M+H+) 272.0.

Workup

  1. additionwas added
  2. extractionthe resulting mixture was extracted with EtOAc
  3. customThe organic solvent was evaporated

Sources & evidence

ORD record
ord-06c7ec98cb4b42128cb4042b6a5381aa
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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