Trifluoroacetic acid → HCID 90320969, compound

HRID 2401262Notes

Reaction equation

HRID 2401262 reaction equation
FC(F)(F)C(O)=O.[O:8]=[C:9]1[N:13]([C:14]2[CH:15]=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=2)[CH2:12][C@H:11]([CH:24]([CH3:26])[CH3:25])[N:10]1[CH2:27][C:28]([O:30]C(C)(C)C)=[O:29]>C(Cl)(Cl)Cl>[O:8]=[C:9]1[N:13]([C:14]2[CH:15]=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=2)[CH2:12][C@H:11]([CH:24]([CH3:26])[CH3:25])[N:10]1[CH2:27][C:28]([OH:30])=[O:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 86705167HCID 86705167, compound

Product 1

HCID 90320969HCID 90320969, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trifluoroacetic acid (30 mL) was added to a solution of tert-butyl {(55)-2-oxo-5-(propan-2-yl)-3-[6-(trifluoromethyl)pyridin-3-yl]imidazolidin-1-yl}acetate (4.44 g) in chloroform (20 mL), and the mixture was stirred at room temperature for 64 hr. Additional trifluoroacetic acid (9 mL) was added thereto, the resulting mixture was further stirred for 1 hr, and the reaction mixture was then concentrated under reduced pressure. A portion (6.5 g) of the residue was dissolved in diethyl ether, followed by extraction with 6M aqueous sodium hydroxide solution and water. The water layer was washed with diethyl ether and then made acidic using 1M hydrochloric acid. After extraction with chloroform, the organic layer was separated out by phase-separation cartridge, and the solvent was distilled off under reduced pressure to afford the title compound (2.3 g).

Workup

  1. stirringthe resulting mixture was further stirred for 1 hr
  2. concentrationthe reaction mixture was then concentrated under reduced pressure
  3. dissolutionA portion (6.5 g) of the residue was dissolved in diethyl ether
  4. extractionfollowed by extraction with 6M aqueous sodium hydroxide solution and water
  5. washThe water layer was washed with diethyl ether
  6. extractionAfter extraction with chloroform
  7. customthe organic layer was separated out by phase-separation cartridge
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e7366cb720974b2495ef2cf56fc4be15
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

Loading…