Ethyl Acetate → HCID 67971457, compound

HRID 1184395Notes

Reaction equation

HRID 1184395 reaction equation
C([O:5][C:6](=[O:31])[CH2:7][NH:8][C:9]([C:11]1[CH:12]=[N:13][C:14]([O:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[CH:16]=1)=[O:10])(C)(C)C.C(OCC)(=O)C>FC(F)(F)C(O)=O.C1(C)C=CC=CC=1.CCCCCCC>[Cl:24][C:19]1[CH:18]=[C:17]([C:15]2[CH:16]=[C:11]([C:9]([NH:8][CH2:7][C:6]([OH:31])=[O:5])=[O:10])[CH:12]=[N:13][C:14]=2[O:25][CH2:26][C:27]([F:30])([F:28])[F:29])[CH:22]=[CH:21][C:20]=1[Cl:23]

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 67970905HCID 67970905, compound

Product 1

HCID 67971457HCID 67971457, compoundYield 98.3%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolventHCID 8900HeptaneSolvent

Procedure

A solution of 4.00 g {[5-(3,4-dichloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-pyridine-3-carbonyl]-amino}-acetic acid tert-butyl ester in 20 ml trifluoroacetic acid was kept at ambient temperature for 30 min. The solvent was evaporated and the residue was dried under high vacuum. The residue was taken up in toluene and the solvent was evaporated to leave a semi solid residue. The residue was taken up in toluene and dichloromethane and the solvents were evaporated to leave a crystalline residue which was taken up in heptane and ethyl acetate and stirred until homogenous slurry was obtained. The solid was collected by filtration, washed with heptane and dried to constant weight to yield 3.47 g of the title compound as white crystalline powder. MS (EI): 422 (M+).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was dried under high vacuum
  3. customthe solvent was evaporated
  4. customto leave a semi solid residue
  5. customdichloromethane and the solvents were evaporated
  6. customto leave a crystalline residue which
  7. customwas obtained
  8. filtrationThe solid was collected by filtration
  9. washwashed with heptane
  10. customdried to constant weight

Sources & evidence

ORD record
ord-78398d67042945e1b73c8c9f191291b7
Source dataset
uspto-grants-2014_03
Patent number
US08669254B2

Reaction notes

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