Acetic Acid → HCID 86605396, compound

HRID 1180429Notes

Reaction equation

HRID 1180429 reaction equation
[Br-].[CH3:2][O:3][C:4]([C@@H:6]([O:11][C@H:12]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[N+:21]([CH2:25][CH2:26][O:27][CH3:28])[CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:14]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:5].C(O)(=O)C>[Pt]=O.C(O)C>[CH3:28][O:27][CH2:26][CH2:25][N:21]1[CH2:22][CH2:23][CH2:24][CH:19]([C:16]2[CH:17]=[CH:18][C:13]([C@@H:12]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[O:11][C@@H:6]([CH2:7][CH:8]([CH3:10])[CH3:9])[C:4]([O:3][CH3:2])=[O:5])=[CH:14][CH:15]=2)[CH2:20]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 69472218HCID 69472218, compound

Product 1

HCID 86605396HCID 86605396, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-{4-[(R)-{[(1S)-1-(methoxycarbonyl)-3-methylbutyl]oxy}(phenyl)methyl]phenyl}-1-(2-methoxyethyl)pyridinium bromide from example 41 step 1 (870 mg, 1.64 mmol), ethanol (50 mL), acetic acid (197 mg, 3.28 mmol) and platinum oxide (hydrated) 79-84% (63 mg) was hydrogenated at 60 psi for 18 hours. The mixture was filtered, concentrated and then concentrated twice with n-heptane. The residue was chromatographed on silica gel using 10% methanol in dichloromethane to obtain the title compound as a thick oil.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. concentrationconcentrated twice with n-heptane
  4. customThe residue was chromatographed on silica gel using 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-5cdc52ad2e0e402893cec7c7a15f6e97
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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