Sodium Hydroxide → HCID 178419905, compound

HRID 733411Notes

Reaction equation

HRID 733411 reaction equation
FC(F)(F)C([N:5]1[CH:10]2[CH2:11][CH2:12][CH:6]1[CH2:7][CH:8]([CH:13]1[C:26]3[CH:25]=[CH:24][C:23]([C:27]4[NH:31][N:30]=[N:29][N:28]=4)=[CH:22][C:21]=3[O:20][C:19]3[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:9]2)=O.[OH-].[Na+]>CO>[NH:31]1[C:27]([C:23]2[CH:24]=[CH:25][C:26]3[CH:13]([CH:8]4[CH2:9][CH:10]5[NH:5][CH:6]([CH2:12][CH2:11]5)[CH2:7]4)[C:14]4[C:19]([O:20][C:21]=3[CH:22]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)=[N:28][N:29]=[N:30]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178521660HCID 178521660, compound2×

Product 1

HCID 178419905HCID 178419905, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,2,2-trifluoro-1-{3-[3-(1H-tetrazol-5-yl)-9H-xanthen-9-yl]-8-aza-bicyclo[3.2.1]oct-8-yl}-ethanone, 4j (0.33 g, 0.724 mmol) in methanol (10 mL) was added a 1N NaOH solution (2.17 mmol, 2.17 mL), and the mixture was heated to reflux for 1 h. The mixture was allowed to cool to rt and evaporated. The residue was purified via reverse phase HPLC (eluent gradient: CH3CN in H2O containing 0.1% TFA) to yield 0.22 g (64%) of title compound 3-[3-(1H-tetrazol-5-yl)-9H-xanthen-9-yl]-8-aza-bicyclo[3.2.1]octane, 5j as a TFA salt. MS m/z (MH+) 360.1.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 h
  3. customevaporated
  4. customThe residue was purified via reverse phase HPLC (eluent gradient: CH3CN in H2O containing 0.1% TFA)

Sources & evidence

ORD record
ord-10caad05dd9443e0846962579dc296bf
Source dataset
uspto-grants-2009_09
Patent number
US07589104B2

Reaction notes

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