Trifluoroacetic acid → HCID 12016228, compound

HRID 2354462Notes

Reaction equation

HRID 2354462 reaction equation
[CH:1]12[CH2:7][CH:4]([NH:5][CH2:6]1)[CH2:3][NH:2]2.F[C:9](F)(F)[C:10]([OH:12])=O.[OH-].[Na+].[C:17]1([O:23][CH3:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH3:24][O:23][C:17]1[CH:22]=[CH:21][C:20]([O:12][C:10]2[CH:9]=[C:6]([N:2]3[CH2:3][C@@H:4]4[CH2:7][C@H:1]3[CH2:6][NH:5]4)[CH:1]=[N:2][CH:3]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 14798Sodium HydroxideHCID 35278102,5-Diazabicyclo[2.2.1]heptane

Product 1

HCID 12016228HCID 12016228, compound

Procedure

To a stirred solution of unpurified (1S,4S)-2-(5-(4-methoxyphenoxy)-3-pyridyl)-5-tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane (0.37 g) in anisole (3.0 mL) at 0-5° C. under a nitrogen atmosphere, trifluoroacetic acid (2.0 mL) was added dropwise over a 10 min. period. After 0.5 h at 0-5° C. the solution was adjusted to pH 5 using 10% NaOH, followed by extraction with diethyl ether (1×10 mL) to remove the anisole. The aqueous portion was adjusted to pH 11 using 10% NaOH, followed by extraction with diethyl ether (3×25 mL). The combined diethyl ether extracts were dried (Na2SO4), filtered and concentrated under vacuum to give a yellow oil (0.26 g). The material was used without further purification.

Workup

  1. extractionfollowed by extraction with diethyl ether (1×10 mL)
  2. customto remove the anisole
  3. extractionfollowed by extraction with diethyl ether (3×25 mL)
  4. dry with materialThe combined diethyl ether extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-799caadc860b4d98b8793ba6e606a719
Source dataset
uspto-grants-2010_07
Patent number
USRE041439E1

Reaction notes

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