1,4-Dioxane hydrochloride → HCID 57665930, compound

HRID 889694Notes

Reaction equation

HRID 889694 reaction equation
[CH2:1]([O:3][C:4](=[O:36])[CH:5]([C:10]1[CH:11]=[C:12]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]=2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2].Cl.O1CCOCC1>CO.[Pt]=O>[CH2:1]([O:3][C:4](=[O:36])[CH:5]([C:10]1[CH:11]=[C:12]([C:26]2[CH:27]=[CH:28][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:30][CH:31]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH:18]([C:22]([F:23])([F:24])[F:25])[NH:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 57665919HCID 57665919, compound

Product 1

HCID 57665930HCID 57665930, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A solution of 4-Methyl-2-[4′-trifluoromethyl-5-(6-trifluoromethyl-pyridin-2-yl)-biphenyl-3-yl]-pentanoic acid ethyl ester, compound 7a (865 mg, 1.7mmol) in MeOH (50 mL), platinum oxide (39.0 mg, 0. 17 mmol) and 4N HCl/dioxane (500 μl) was hydrogenated at 20 psi for 4 hours. The reaction mixture was filtered through celite, washed with MeOH and concentrated in vacuo. The residue was partitioned between dichloromethane and Na2CO3 to give the free base. Purification by silica gel chromatography gave the desired product (813 mg, 93%) (M+H) 515.53, Found 516.3.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with MeOH
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between dichloromethane and Na2CO3
  5. customto give the free base
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-d0d18572efd448d09ce79b3d3ef50610
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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