Trifluoroacetic acid → HCID 9882696, compound

HRID 2354464Notes

Reaction equation

HRID 2354464 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]=[C:21]([CH:20]=[CH:19][CH:18]=1)[O:12][C:10]1[CH:9]=[C:6]([N:2]2[CH2:3][CH:4]3[CH2:7][CH:1]2[CH2:6][NH:5]3)[CH:1]=[N:2][CH:3]=1

Participants

5

Reactant 4

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

Product 1

HCID 9882696HCID 9882696, compoundYield 82%

Procedure

To a stirred solution of (1S,4S)-5-(5-(3-methoxyphenoxy)-3-pyridyl)-2-tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane (0.62 g, 1.5 mmol) in anisole (3.5 mL) at 0-5° C. and under a nitrogen atmosphere, trifluoroacetic acid (2.5 mL) was added drop-wise over a 10 min period. After 0.5 h at 25° C., the solution was adjusted to pH 5 using 10% NaOH, followed by extraction with diethyl ether (1×15 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 colorless oil (0.41 g, 82%).

Workup

  1. extractionfollowed by extraction with diethyl ether (1×15 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-149fae90fa124e61b55475943691f487
Source dataset
uspto-grants-2010_07
Patent number
USRE041439E1

Reaction notes

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