HCID 68564096, compound → N-(4-tert-butyl-benzyl)-N-[2-(3-tert-butyl-4-hydroxy-phenyl)-ethyl]-3-chloro-2-fluoro-5-trifluoromethyl-benzamide

HRID 19817Notes

Reaction equation

HRID 19817 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N:17]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:35][CH:34]=2)[C:18](=[O:31])[C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([Cl:29])[C:20]=2[F:30])=[CH:11][C:10]=1[C:43]([CH3:46])([CH3:45])[CH3:44])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[C:39]([C:36]1[CH:35]=[CH:34][C:33]([CH2:32][N:17]([CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([C:43]([CH3:46])([CH3:45])[CH3:44])[CH:11]=2)[C:18](=[O:31])[C:19]2[CH:24]=[C:23]([C:25]([F:27])([F:26])[F:28])[CH:22]=[C:21]([Cl:29])[C:20]=2[F:30])=[CH:38][CH:37]=1)([CH3:40])([CH3:42])[CH3:41]

Participants

4

Reactant 1

HCID 68564096HCID 68564096, compound

Product 1

HCID 86613998N-(4-tert-butyl-benzyl)-N-[2-(3-tert-butyl-4-hydroxy-phenyl)-ethyl]-3-chloro-2-fluoro-5-trifluoromethyl-benzamideYield 82.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 182 mg of N-[2-(4-benzyloxy-3-tert-butyl-phenyl)-ethyl]-N-(4-tert-butyl-benzyl)-3-chloro-2-fluoro-5-trifluoromethyl-benzamide (0.278 mmol) in 15 ml ethyl acetate were hydrogenated over 100 mg Pd/C-5%. After completion of the reaction the suspension was filtered off and concentrated in vacuo. The resulting residue was purified by flash column chromatography (Heptane/AcOEt:90/10) to yield 130 mg of a colorless viscous oil. MS (ISP) 564 (M+H)+.

Workup

  1. customAfter completion of the reaction the suspension
  2. filtrationwas filtered off
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by flash column chromatography (Heptane/AcOEt:90/10)

Sources & evidence

ORD record
ord-5e73ff236b9a4c618e8f5e9b3d9c2c94
Source dataset
uspto-grants-2010_06
Patent number
US07745477B2

Reaction notes

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