Nitrogen → 5-(3-Carboxy-phenyl)-oxazole-4-carboxylic acid methyl ester

HRID 42788Notes

Reaction equation

HRID 42788 reaction equation
N#N.[CH3:3][O:4][C:5]([C:7]1[N:8]=[CH:9][O:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([O:20]C(C)(C)C)=[O:19])[CH:13]=1)=[O:6]>C(O)(C(F)(F)F)=O>[CH3:3][O:4][C:5]([C:7]1[N:8]=[CH:9][O:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([OH:20])=[O:19])[CH:13]=1)=[O:6]

Participants

4

Reactant 2

HCID 947NitrogenHCID 669291745-(3-Tert-butoxycarbonyl-phenyl)-oxazole-4-carboxylic acid methyl ester

Product 1

HCID 669293005-(3-Carboxy-phenyl)-oxazole-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(3-tert-butoxycarbonyl-phenyl)-oxazole-4-carboxylic acid methyl ester (1.00 g, 3.30 mmol) in TFA (13.3 mL) was stirred at rt for 45 min. The TFA was removed under reduced pressure and the residue was triturate in Et2O, filtered and washed with Et2O to give the title compound as a white powder. LC-MS-conditions 02: tR=0.79 min, [M+H]+=248.20.

Workup

  1. customThe TFA was removed under reduced pressure
  2. customthe residue was triturate in Et2O
  3. filtrationfiltered
  4. washwashed with Et2O

Sources & evidence

ORD record
ord-8dd96036e5284797b51c53fd94385bb7
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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