Hippuric Acid → (Z)-methyl 2-fluoro-6-((5-oxo-2-phenyloxazol-4(5H)-ylidene)methyl)benzoate

HRID 1476810Notes

Reaction equation

HRID 1476810 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]=O)[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:14]([NH:22][CH2:23][C:24]([OH:26])=[O:25])(=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])(=O)C.[Na+]>C(OC(=O)C)(=O)C.CCOC(C)=O>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8](/[CH:12]=[C:23]2\[N:22]=[C:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[O:26][C:24]\2=[O:25])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 464Hippuric AcidHCID 517045Sodium AcetateHCID 87166864Methyl 2-fluoro-6-formylbenzoate

Product 1

HCID 90387079(Z)-methyl 2-fluoro-6-((5-oxo-2-phenyloxazol-4(5H)-ylidene)methyl)benzoate

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolventHCID 8857Ethyl AcetateSolvent

Procedure

This step was performed in five separate batches. For each batch, a solution of methyl 2-fluoro-6-formylbenzoate (3 g, 16.5 mmol), 2-benzamidoacetic acid (3.6, 20 mmol) and sodium acetate (1.62 g, 19.7 mmol) in acetic anhydride (30 mL) was heated at 100° C. in a microwave reactor (100 W, 150 psi) under nitrogen atmosphere for 2 hours. The reaction mixtures were diluted with EtOAc (100 mL) and washed with saturated aqueous Na2CO3. The combined organic layers were concentrated in vacuo to give the title compound as a brown solid, which was used without further purification (15 g). ESI-MS m/z [M+H]+ 326.2.

Workup

  1. customseparate batches
  2. customThe reaction mixtures
  3. washwashed with saturated aqueous Na2CO3
  4. concentrationThe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-a7efcbd0808f4a09b7f10f09191181cd
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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