benzyl 4'-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethylamino]ethoxy)-3',5'-dimethylbiphenyl-4-carboxylate → HCID 68540748, compound

HRID 2243545Notes

Reaction equation

HRID 2243545 reaction equation
[OH:1][C@H:2]([C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)[C@@H:3]([NH:5][CH2:6][CH2:7][O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24]CC3C=CC=CC=3)=[O:23])=[CH:18][CH:17]=2)=[CH:11][C:10]=1[CH3:32])[CH3:4]>CN(C)C=O.[C].[Pd]>[OH:1][C@H:2]([C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)[C@@H:3]([NH:5][CH2:6][CH2:7][O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][CH:17]=2)=[CH:11][C:10]=1[CH3:32])[CH3:4]

Participants

4

Reactant 1

HCID 68544588benzyl 4'-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethylamino]ethoxy)-3',5'-dimethylbiphenyl-4-carboxylate

Product 1

HCID 68540748HCID 68540748, compoundYield 27.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of benzyl 4′-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethylamino]ethoxy}-3′,5′-dimethyl -biphenyl-4-carboxylate (0.108 g) and 10% palladium-carbon (50% wet, 0.05 g) in N,N-dimethylformamide (4 mL) was stirred at room temperature for 1.5 hrs under an atmosphere of hydrogen. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo. Methylene chloride was added to the residue. The resulting precipitate was collected by filtration, and purified by octadecyl silica gel column chromatography (eluent: acetonitrile/water=1/1) to afford the title compound (0.025 g) as a white amorphous. The structure and physical data were shown in table 1.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionMethylene chloride was added to the residue
  4. filtrationThe resulting precipitate was collected by filtration
  5. custompurified by octadecyl silica gel column chromatography (eluent: acetonitrile/water=1/1)

Sources & evidence

ORD record
ord-6379c42759c64ee38c66b437b95f292c
Source dataset
uspto-grants-2010_03
Patent number
US07674938B2

Reaction notes

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