Potassium Carbonate → 2-Amino-5-oxazol-5-yl-4-trifluoromethyl-benzoic acid methyl ester

HRID 906632Notes

Reaction equation

HRID 906632 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([CH:10]=[O:11])[C:7]([C:12]([F:15])([F:14])[F:13])=[CH:6][C:5]=1[NH:16]C(=O)C.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S([CH2:36][N+:37]#[C-:38])(=O)=O)=CC=1>CO>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([C:10]2[O:11][CH:38]=[N:37][CH:36]=2)[C:7]([C:12]([F:13])([F:14])[F:15])=[CH:6][C:5]=1[NH2:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 591644232-Acetylamino-5-formyl-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 119646012-Amino-5-oxazol-5-yl-4-trifluoromethyl-benzoic acid methyl esterYield 28.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Acetylamino-5-formyl-4-trifluoromethyl-benzoic acid methyl ester (880 mg, 3.043 mmol) in MeOH (10 mL) was treated with potassium carbonate (463 mg, 3.35 mmol) and toluene-4-sulfonyl methylisocyanide (594 mg, 3.04 mmol) and the mixture was refluxed for 5 h. The reaction mixture was cooled to r.t., concentrated in vacuo and the residue was purified by flash chromatography (100 g silica gel, DCM) to give the title product (248 mg, 28%) as a yellow powder. API-ES: m/z 287.1 [M+H]+, rt 4.40 min.

Workup

  1. temperaturethe mixture was refluxed for 5 h
  2. concentrationconcentrated in vacuo
  3. customthe residue was purified by flash chromatography (100 g silica gel, DCM)

Sources & evidence

ORD record
ord-fbd9e548ecc54ebc85cbf2102e7a3a0b
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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