HCID 69595896, compound → HCID 69595809, compound

HRID 719392Notes

Reaction equation

HRID 719392 reaction equation
C([O:8][N:9]1[C@@H:13]([CH:14]([CH3:16])[CH3:15])[CH2:12][C@@H:11]([N:17]([CH2:37][CH2:38][CH3:39])[S:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C:10]1=[O:40])C1C=CC=CC=1>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[OH:8][N:9]1[C@@H:13]([CH:14]([CH3:16])[CH3:15])[CH2:12][C@@H:11]([N:17]([CH2:37][CH2:38][CH3:39])[S:18]([C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:29][CH:28]=3)=[CH:25][CH:26]=2)(=[O:20])=[O:19])[C:10]1=[O:40]

Participants

4

Reactant 1

HCID 69595896HCID 69595896, compound

Product 1

HCID 69595809HCID 69595809, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent

Procedure

N-[(3R,5R)-1-(Benzyloxy)-5-isopropyl-2-oxopyrrolidinyl]-N-propyl-4′-(trifluoromethyl)[1,1′-biphenyl]-4-sulfonamide (0.015 g, 0.026 mmoles, Example 28b) in 5.0 mL methanol was hydrogenated on 5% Pd/BaSO4 (0.005 g) at 1 atm H2 and 22° C. After 6 hours the solution was filtered through Celite and concentrated by rotary evaporation to afford 0.012 g (95% yield) of the title compound as a white solid. LC-MS (APCI) m/z 485 (M+1). 1H NMR (CD3OD) δ 8.07 (d, J=8 Hz, 2H), 7.89 (d, J=6 Hz, 2H), 7.87 (d, J=6 Hz, 2H), 7.79 (d, J=8 Hz, 2H), 4.69 (t, J=10 Hz, 1H), 3.57 (ddd, J1=4 Hz, J2=7 Hz, J3=10 Hz, 1H), 3.10 (t, J=8 Hz, 2H), 2.30–2.18 (m, 2H), 1.81–1.57 (m's, 3H), 0.95 (d, J=7 Hz, 3H), 0.90 (d, J=7 Hz, 3H) and 0.85 (t, J=8 Hz, 3H) ppm.

Workup

  1. filtrationAfter 6 hours the solution was filtered through Celite
  2. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-0ff14099e0bd411c8e52dd3eeb705b09
Source dataset
uspto-grants-2006_11
Patent number
US07132434B2

Reaction notes

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