HCID 58618748, compound → HCID 21022005, compound

HRID 1794224Notes

Reaction equation

HRID 1794224 reaction equation
C([O:3][C:4]([C@@H:6]1[O:11][C:10]2[CH:12]=[CH:13][C:14]([CH2:16][C@H:17]([NH:19][CH2:20][C@H:21]([OH:38])[CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([O:30]CC4C=CC=CC=4)=[CH:26][CH:25]=3)[CH3:18])=[CH:15][C:9]=2[O:8][CH2:7]1)=[O:5])C>C(O)C.[C].[Pd]>[OH:38][C@H:21]([CH2:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=1)[CH2:20][NH:19][C@H:17]([CH3:18])[CH2:16][C:14]1[CH:13]=[CH:12][C:10]2[O:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7][O:8][C:9]=2[CH:15]=1

Participants

4

Reactant 1

HCID 58618748HCID 58618748, compound

Product 1

HCID 21022005HCID 21022005, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 6-[2-(R)-[3-(4-benzyloxyphenoxy)-2-(S)-hydroxypropylamino]propyl-2,3-dihydro-1,4-benzodioxine-2-(R)-carboxylic acid ethyl ester obtained in Example 11 (270 mg) in ethanol (20 mL) was added 10% palladium-carbon (50 mg). This solution was stirred under hydrogen atmosphere at room temperature for 16 hours. After filtration through Celite, the filtrate was concentrated under reduced pressure. A solution of the residue in 1N—HCl (8 mL) was stirred at 100° C. for 5 hours. After allowing to cool to room temperature, it was concentrated to dryness under reduced pressure. The residue was dissolved in water/acetonitrile=1/1 (v/v) (10 mL), and the pH was adjusted to 6.3 by addition of saturated aqueous sodium bicarbonate. It was concentrated under reduced pressure, the residue was purified by HP column chromatography and the title compound (209 mg) was obtained from the effluent with water/methanol=40/60 (v/v). Yield: 85%

Workup

  1. filtrationAfter filtration through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. stirringA solution of the residue in 1N—HCl (8 mL) was stirred at 100° C. for 5 hours
  4. temperatureto cool to room temperature
  5. concentrationit was concentrated to dryness under reduced pressure
  6. dissolutionThe residue was dissolved in water/acetonitrile=1/1 (v/v) (10 mL)
  7. additionthe pH was adjusted to 6.3 by addition of saturated aqueous sodium bicarbonate
  8. concentrationIt was concentrated under reduced pressure
  9. customthe residue was purified by HP column chromatography

Sources & evidence

ORD record
ord-3776929c48d544cf9dd55655207f491a
Source dataset
uspto-grants-2006_04
Patent number
US07022732B2

Reaction notes

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