HCID 178435522, compound → HCID 178435520, compound

HRID 2211398Notes

Reaction equation

HRID 2211398 reaction equation
[CH2:1]([C:3]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[C:24]([O:34]CC2C=CC=CC=2)=[CH:23][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:17][C:18]1[NH:22][N:21]=[N:20][N:19]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([C:3]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[C:24]([OH:34])=[CH:23][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:17][C:18]1[NH:22][N:21]=[N:20][N:19]=1)[CH3:2]

Participants

4

Reactant 1

HCID 178435522HCID 178435522, compound

Product 1

HCID 178435520HCID 178435520, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-(2-(2-(3-(2-Ethyl-4-(4-fluorophenyl)-5-benzyloxyphenoxy)propoxy)phenyl)ethyl)-1H-tetrazole (90 mg, 0.16 mmol) was dissolved in ethanol and 10% palladium on carbon catalyst was added under an atmosphere of carbon dioxide. The mixture was then hydrogenated at 30 psi at room temperature for 1 hour. The catalyst was filtered off and the solution evaporated to dryness to give an oil. This oil was then purified by reverse phase HPLC on a C18 column eluting with methanol/water (90:10) containing 0.01% acetic acid. The title compound was isolated as an oil (yield 41 mg, 55%) containing 0.3 equivalents of acetic acid. NMR, MS.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solution evaporated to dryness
  3. customto give an oil
  4. customThis oil was then purified by reverse phase HPLC on a C18 column
  5. washeluting with methanol/water (90:10)
  6. additioncontaining 0.01% acetic acid

Sources & evidence

ORD record
ord-4a423a4827774d3782b4afe7e74e5ccc
Source dataset
uspto-grants-1995_10
Patent number
US05462954

Reaction notes

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