HCID 69201908, compound → 4'-{2-[(1S,2R)-2-Hydroxy-2-(4-hydroxy-3-methanesulfonylaminophenyl)-1-methylethylamino]ethoxy}-3',5'-dimethylbiphenyl-4-carboxylic acid

HRID 2220657Notes

Reaction equation

HRID 2220657 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([OH:46])[C@@H:16]([NH:18][CH2:19][CH2:20][O:21][C:22]2[C:27]([CH3:28])=[CH:26][C:25]([C:29]3[CH:34]=[CH:33][C:32]([C:35]([O:37]CC4C=CC=CC=4)=[O:36])=[CH:31][CH:30]=3)=[CH:24][C:23]=2[CH3:45])[CH3:17])=[CH:11][C:10]=1[NH:47][S:48]([CH3:51])(=[O:50])=[O:49])C1C=CC=CC=1>CN(C)C=O.[C].[Pd]>[OH:46][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:47][S:48]([CH3:51])(=[O:50])=[O:49])[CH:11]=1)[C@@H:16]([NH:18][CH2:19][CH2:20][O:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([OH:37])=[O:36])=[CH:31][CH:30]=2)=[CH:24][C:23]=1[CH3:45])[CH3:17]

Participants

4

Reactant 1

HCID 69201908HCID 69201908, compound

Product 1

HCID 692010834'-{2-[(1S,2R)-2-Hydroxy-2-(4-hydroxy-3-methanesulfonylaminophenyl)-1-methylethylamino]ethoxy}-3',5'-dimethylbiphenyl-4-carboxylic acidYield 65.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of benzyl 4′-{2-[(1S,2R)-2-(4-benzyloxy-3-methanesulfonylaminophenyl)-2-hydroxy-1-methylethylamino]ethoxy}-3′,5′-dimethylbiphenyl-4-carboxylate (0.074 g) in N,N-dimethylformamide (4 mL) was added 10% palladium-carbon (0.05 g), and the mixture was stirred at room temperature for 1.5 hrs under an atmosphere of hydrogen. The catalyst was removed by filtration, and the solvent was evaporated under reduced pressure. Methylene chloride was added to the residue, and the resulting precipitated materials were collected by filtration. The crude product was purified by ODS column chromatography (eluent: acetonitrile/water=1/1) to afford the title compound (0.036 g).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. additionMethylene chloride was added to the residue
  4. customthe resulting precipitated materials
  5. filtrationwere collected by filtration
  6. customThe crude product was purified by ODS column chromatography (eluent: acetonitrile/water=1/1)

Sources & evidence

ORD record
ord-f9ab299eb7f74fb3b504ee48d301918b
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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