Trifluoroacetic acid → Ethyl 3-(5-(2-formyl-3-hydroxy-5-(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405257Notes

Reaction equation

HRID 405257 reaction equation
C(O)(C(F)(F)F)=O.[CH:8]([C:10]1[C:15]([O:16]COC)=[CH:14][C:13]([C:20]([F:23])([F:22])[F:21])=[CH:12][C:11]=1[C:24]1[CH:25]=[CH:26][C:27]([C:30]([NH:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:31])=[N:28][CH:29]=1)=[O:9]>C(Cl)Cl>[CH:8]([C:10]1[C:15]([OH:16])=[CH:14][C:13]([C:20]([F:21])([F:22])[F:23])=[CH:12][C:11]=1[C:24]1[CH:25]=[CH:26][C:27]([C:30]([NH:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:31])=[N:28][CH:29]=1)=[O:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86674289Ethyl 3-(5-(2-formyl-3-(methoxymethoxy)-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Product 1

HCID 86674288Ethyl 3-(5-(2-formyl-3-hydroxy-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Neat TFA (1 mL) was added to a DCM solution (3 mL) of ethyl 3-(5-(2-formyl-3-(methoxymethoxy)-5-(trifluoromethyl)phenyl)picolinamido)propanoate (121 mg, 0.27 mmol) and the resulting mixture was stirred at room temperature. After 1 h the resulting mixture was concentrated to yield the title compound, which was used in the next step without further purification.

Workup

  1. concentrationAfter 1 h the resulting mixture was concentrated

Sources & evidence

ORD record
ord-3c4acc5685b74662999a442f8ae34b14
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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