HCID 69414949, compound → HCID 12094760, compound

HRID 1350915Notes

Reaction equation

HRID 1350915 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([OH:34])[CH2:16][NH:17][C:18]([CH3:33])([CH3:32])[CH2:19][CH2:20][N:21]2[CH:25]=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:23]=[CH:22]2)=[CH:11][C:10]=1[NH:35][S:36]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)(=[O:38])=[O:37])C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH3:33][C:18]([NH:17][CH2:16][C@@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:35][S:36]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)(=[O:38])=[O:37])[CH:11]=1)[OH:34])([CH3:32])[CH2:19][CH2:20][N:21]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:23]=[CH:22]1

Participants

5

Reactant 2

HCID 69414949HCID 69414949, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12094760HCID 12094760, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.10 g palladium (5% on activated charcoal) were added to. a solution of 0.30 g (0.41 mmol) (R)—N-(2-benzyloxy-5-{2-[1,1-dimethyl-3-(4-phenylimidazol-1-yl)-propylamino]-1-hydroxyethyl)phenyl)-benzenesulphonamide in 15 mL ethanol. The reaction mixture was shaken in an autoclave under a hydrogen pressure of 20 psi at ambient temperature for 3 h. The hydrogen pressure was released, the palladium was filtered off and the filtrate was freed from solvent using the rotary evaporator. The residue was purified by flash column chromatography [methylene chloride/methanol/ammonia (90:10:1)]. 0.20 g (0.31 mmol, 75%) (R)—N-(5-{2-[1,1-dimethyl-3-(4-phenylimidazol-1-yl)-propylamino]-1-hydroxyethyl}-2-hydroxy-phenyl)-benzenesulphonamide was obtained as a colourless solid.

Workup

  1. filtrationthe palladium was filtered off
  2. customthe rotary evaporator
  3. customThe residue was purified by flash column chromatography [methylene chloride/methanol/ammonia (90:10:1)]

Sources & evidence

ORD record
ord-e4746b2db4a24cbe9206ba1baf129c0f
Source dataset
uspto-grants-2007_05
Patent number
US07214698B2

Reaction notes

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