HCID 69595822, compound → HCID 69595887, compound

HRID 719390Notes

Reaction equation

HRID 719390 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 69595822HCID 69595822, compound

Product 1

HCID 69595887HCID 69595887, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent

Procedure

N-[(3R,5S)-1-(Benzyloxy)-5-isopropyl-2-oxopyrrolidinyl]-N-propyl-4′-(trifluoromethyl)[1,1′-biphenyl]-4-sulfonamide (0.023 g, 0.040 mmoles, Example 28a) 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 0.019 g (98% yield) of the title compound as a white solid. LC-MS (APCI) n/z 485 (M+1). 1H NMR (DMSO-d6) δ 9.90 (br s, 1H), 8.04 (d, J=8 Hz, 2H), 7.99 (d, J=8 Hz, 2H), 7.97 (d, J=8 Hz, 2H), 7.88 (d, J=8 Hz, 2H), 4.53 (dd, J1=8 Hz, J2=10 Hz, 1H), 3.62 (dt, J1=3 Hz, J2=9 Hz, 1H), 3.08–2.90 (sym m, 2H), 2.14–2.02 (sym m, 2H), 1.87 (ddd, J1=8 Hz, J2=9 Hz, J3=14 Hz, 1H), 1.67–1.49 (sym m, 2H), 0.86 (d, J=7 Hz, 3H), 0.80 (t, J=7 Hz, 3H) and 0.77 (d, J=7 Hz, 3H) ppm.

Workup

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

Sources & evidence

ORD record
ord-14545eeed42849c0973858f7bdbb90a1
Source dataset
uspto-grants-2006_11
Patent number
US07132434B2

Reaction notes

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