HCID 131720757, compound → HCID 131720756, compound

HRID 1955781Notes

Reaction equation

HRID 1955781 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:18]([NH:26][CH2:27][CH:28]([C:30]2[CH:31]=[CH:32][C:33]([O:41]CC3C=CC=CC=3)=[C:34]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[CH:35]=2)[OH:29])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17].[H][H]>[Pd].CO>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:18]([NH:26][CH2:27][CH:28]([C:30]2[CH:31]=[CH:32][C:33]([OH:41])=[C:34]([NH:36][S:37]([CH3:40])(=[O:38])=[O:39])[CH:35]=2)[OH:29])[CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

Participants

5

Reactant 2

HCID 131720757HCID 131720757, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131720756HCID 131720756, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-[5-[2-[[1-(3,4-Dimethoxyphenyl)-2-phenylethyl]amino]-1-hydroxyethyl]-2-(phenylmethoxy)phenyl]methanesulfonamide, trifluoroacetate salt (220 mg, 0.38 mmol) was hydrogenated using 10% Pd/C (120 mg) and MeOH (25 mL, AR grade) at 40 psi of hydrogen in a Parr apparatus for one hour at room temperature. The catalyst was filtered through Celite and washed with MeOH. The filtrate and MeOH washings were combined and concentrated to afford 178 mg (0.37 mmol, 96% yield) of the title compound as a pale yellow crystalline powder. The title compound is a racemic mixture of diastereomers.

Workup

  1. customfor one hour
  2. customat room temperature
  3. filtrationThe catalyst was filtered through Celite
  4. washwashed with MeOH
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-812853d83db24d749d35844aa147a026
Source dataset
uspto-grants-1998_07
Patent number
US05776983

Reaction notes

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