1-{4-[5-(2-Fluoro-biphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]-benzyl}-4-(morpholine-4-carbonyl)-piperidine-4-carboxylic acid benzyl ester → 1-{4-[5-(2-Fluoro-biphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]-benzyl}-4-(morpholine-4-carbonyl)-piperidine-4-carboxylic acid

HRID 2407512Notes

Reaction equation

HRID 2407512 reaction equation
C([O:8][C:9]([C:11]1([C:42]([N:44]2[CH2:49][CH2:48][O:47][CH2:46][CH2:45]2)=[O:43])[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[N:28]=[C:27]([C:29]4[CH:34]=[CH:33][C:32]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)=[C:31]([F:41])[CH:30]=4)[O:26][N:25]=3)=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)=[O:10])C1C=CC=CC=1>C(OCC)(=O)C.O1CCCC1.C(O)C.[Pd]>[F:41][C:31]1[CH:30]=[C:29]([C:27]2[O:26][N:25]=[C:24]([C:21]3[CH:20]=[CH:19][C:18]([CH2:17][N:14]4[CH2:13][CH2:12][C:11]([C:42]([N:44]5[CH2:45][CH2:46][O:47][CH2:48][CH2:49]5)=[O:43])([C:9]([OH:10])=[O:8])[CH2:16][CH2:15]4)=[CH:23][CH:22]=3)[N:28]=2)[CH:34]=[CH:33][C:32]=1[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 1

HCID 595094421-{4-[5-(2-Fluoro-biphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]-benzyl}-4-(morpholine-4-carbonyl)-piperidine-4-carboxylic acid benzyl ester

Product 1

HCID 595094981-{4-[5-(2-Fluoro-biphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]-benzyl}-4-(morpholine-4-carbonyl)-piperidine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18365940Tetrahydrofuran ethyl acetate ethanolSolvent

Procedure

Pd/C (0.13 g) is added to a solution of 1-{4-[5-(2-fluoro-biphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]-benzyl}-4-(morpholine-4-carbonyl)-piperidine-4-carboxylic acid benzyl ester (0.43 g, 0.0006 mol) in a mixture of ethyl acetate:tetrahydrofuran:ethanol (3:2:3, 45 mL). Hydrogen gas is bubbled through the reaction mixture under stirring at room temperature for 2 hrs. The reaction mixture is filtered through a celite bed, washed with MDC:MeOH (80:20, 100 mL) and the filtrate is concentrated under reduced pressure to get solid mass, which is purified by column chromatography (silica gel 230-400 mesh, MDC:MeOH 8:2) to get 1-{4-[5-(2-fluoro-biphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]-benzyl}-4-(morpholine-4-carbonyl)-piperidine-4-carboxylic acid.

Workup

  1. customHydrogen gas is bubbled through the reaction mixture
  2. filtrationThe reaction mixture is filtered through a celite bed
  3. washwashed with MDC
  4. concentrationMeOH (80:20, 100 mL) and the filtrate is concentrated under reduced pressure
  5. customto get solid mass, which
  6. customis purified by column chromatography (silica gel 230-400 mesh, MDC:MeOH 8:2)

Sources & evidence

ORD record
ord-8812155a988e4736be783c8cff22e0db
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

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