Trifluoroacetic acid → HCID 86709404, compound

HRID 2172268Notes

Reaction equation

HRID 2172268 reaction equation
[F:1][C:2]([F:7])([F:6])C(O)=O.C(O[C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][C@@H:29]3[O:34][C:33]4=[N:35][C:36]([N+:38]([O-:40])=[O:39])=[CH:37][N:32]4[CH2:31][CH2:30]3)=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>>[N+:38]([C:36]1[N:35]=[C:33]2[N:32]([CH:37]=1)[CH2:31][CH2:30][C@H:29]([CH2:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([CH:18]3[CH2:19][CH2:20][N:15]([CH2:13][C:21]4[CH:26]=[CH:25][C:24]([O:27][C:2]([F:1])([F:6])[F:7])=[CH:23][CH:22]=4)[CH2:16][CH2:17]3)=[CH:22][CH:23]=1)[O:34]2)([O-:40])=[O:39]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70874498HCID 70874498, compound

Product 1

HCID 86709404HCID 86709404, compound

Procedure

Trifluoroacetic acid (6 ml) was added to 4-[4-((R)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-7-ylmethoxy)phenyl]piperidine-1-carboxylic acid tert-butyl ester (2.0 g), and the mixture was stirred at room temperature for 40 minutes. The reaction mixture was concentrated under reduced pressure. Methylene chloride (6 ml) and triethylamine (6 ml) were added to the residue, and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was reconcentrated under reduced pressure. N-Methylpyrrolidone (6 ml), 4-(trifluoromethoxy)benzaldehyde (0.93 ml) and sodium triacetoxyborohydride (1.39 g) were added to the residue, and the mixture was stirred at room temperature for 3 hours. A 20% sodium carbonate aqueous solution (20 ml) and water (20 ml) were added to the reaction mixture, followed by stirring. The insoluble matter generated was collected by filtration. The residue thus obtained was washed with water and hexane, and then dried. Subsequently, the residue was suspended in ethyl acetate-isopropyl ether (1:1), and the suspension was stirred at room temperature, followed by collection by filtration. The residue was then dried to afford the title compound as a reddish brown solid (2.39 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionMethylene chloride (6 ml) and triethylamine (6 ml) were added to the residue
  3. stirringthe mixture was stirred at room temperature for 10 minutes
  4. additionN-Methylpyrrolidone (6 ml), 4-(trifluoromethoxy)benzaldehyde (0.93 ml) and sodium triacetoxyborohydride (1.39 g) were added to the residue
  5. stirringthe mixture was stirred at room temperature for 3 hours
  6. additionA 20% sodium carbonate aqueous solution (20 ml) and water (20 ml) were added to the reaction mixture
  7. stirringby stirring
  8. filtrationThe insoluble matter generated was collected by filtration
  9. customThe residue thus obtained
  10. washwas washed with water and hexane
  11. customdried
  12. stirringthe suspension was stirred at room temperature
  13. filtrationfollowed by collection by filtration
  14. customThe residue was then dried

Sources & evidence

ORD record
ord-3466558cf88c439197e0dbabac0564d3
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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