HCID 66615893, compound → 4-(4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-butyric acid

HRID 76038Notes

Reaction equation

HRID 76038 reaction equation
C([O:8][C:9](=[O:38])/[CH:10]=[CH:11]/[CH2:12][CH:13]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[O:29][C:28]([NH:30][C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=4)=[N:27][CH:26]=3)=[CH:21][CH:20]=2)[CH2:15][CH2:14]1)C1C=CC=CC=1>CCOC(C)=O.CCO.[OH-].[OH-].[Pd+2]>[Cl:37][C:33]1[CH:32]=[C:31]([NH:30][C:28]2[O:29][C:25]([C:22]3[CH:23]=[CH:24][C:19]([CH:16]4[CH2:15][CH2:14][CH:13]([CH2:12][CH2:11][CH2:10][C:9]([OH:38])=[O:8])[CH2:18][CH2:17]4)=[CH:20][CH:21]=3)=[CH:26][N:27]=2)[CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 1

HCID 66615893HCID 66615893, compound

Product 1

HCID 578990884-(4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-butyric acidYield 86.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of (E)-4-(4-{4-[2-(3-chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-but-2-enoic acid benzyl ester (139 mg, 0.283 mmol) in EtOAc/EtOH (5:1 v/v, 6 mL) is added Pd(OH)2 (100 mg) the mixture is stirred in an hydrogenated at 1 atm for 72 h. The catalyst is filtered and washed with EtOAc. The filtrated is then concentrated and dried under high vacuum to give the title compound (107 mg) as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 0.98-1.09 (m, 2H) 1.18-1.25 (m, 2H) 1.39-1.48 (m, 2H) 1.49-1.57 (m, 2H) 1.82 (d, J=10.11 Hz, 4H) 1.74-1.85 (m, 1H) 2.18 (t, J=7-33 Hz, 2H) 6.99 (ddd, J=7.96, 2.02, 0.88 Hz, 1H) 7.28-7.33 (m, 3H) 7.40 (s, 1H) 7.47-7.52 (m, 3H) 7.85 (t, J=2.02 Hz, 1H); (M+H)+=439.0.

Workup

  1. filtrationThe catalyst is filtered
  2. washwashed with EtOAc
  3. concentrationThe filtrated is then concentrated
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-89f72d33df90437bb9d09ebe8d4abe12
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

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