HCID 67486053, compound → HCID 67486504, compound

HRID 2371253Notes

Reaction equation

HRID 2371253 reaction equation
C([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([C:37]2[CH:42]=[CH:41][C:40]([C:43]([CH3:46])([CH3:45])[CH3:44])=[CH:39][CH:38]=2)[C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:25][CH:24]=2)=[O:21])=[CH:14][CH:13]=1)C1C=CC=CC=1>[Pd].CO.C(OCC)(=O)C>[C:43]([C:40]1[CH:39]=[CH:38][C:37]([CH:19]([CH2:18][C:15]2[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][OH:8])=[CH:13][CH:14]=2)[C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:25][CH:24]=2)=[O:21])=[CH:42][CH:41]=1)([CH3:46])([CH3:44])[CH3:45]

Participants

4

Reactant 1

HCID 67486053HCID 67486053, compound

Product 1

HCID 67486504HCID 67486504, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of 3-[4-(2-Benzyloxyethoxy)-phenyl]-2-(4-tert-butylphenyl)-N-(4-cyclohexylmethoxyphenyl)-propionamide (200 mg, 0.32 mmol) and 10% Pd/C (20 mg) in a solution of methanol/ethyl acetate (60 mL, 4:1) was stirred under an atmosphere of H2 overnight. The mixture was filtered through celite and concentrated under vacuum. The crude was purified by chromatography on silica gel (ISCO cartridge, 40 g), eluting with dichloromethane over 20 minutes to afford 2-(4-tert-Butylphenyl)-N-(4-cyclohexylmethoxyphenyl)-3-[4-(2-hydroxy ethoxy)-phenyl]-propionamide (126 mg, 74%). LC-MS m/z=530 [C34H43NO4+H]+.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationconcentrated under vacuum
  3. customThe crude was purified by chromatography on silica gel (ISCO cartridge, 40 g)
  4. washeluting with dichloromethane over 20 minutes

Sources & evidence

ORD record
ord-6f3bcc7e37e242ce81db1044d96f01b4
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

Loading…