HCID 68433575, compound → HCID 68433471, compound

HRID 2242658Notes

Reaction equation

HRID 2242658 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:28]([N:30]1[CH2:34][CH2:33][C:32]([F:36])([F:35])[CH2:31]1)=[O:29])[C@H:10]([C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:26][CH2:25][CH2:24][C:23]2=[O:27])=[CH:18][CH:17]=1)[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)(=O)C.[Pt](=O)=O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:28]([N:30]1[CH2:34][CH2:33][C:32]([F:36])([F:35])[CH2:31]1)=[O:29])[C@H:10]([CH:16]1[CH2:21][CH2:20][CH:19]([N:22]2[CH2:26][CH2:25][CH2:24][C:23]2=[O:27])[CH2:18][CH2:17]1)[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 68433575HCID 68433575, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68433471HCID 68433471, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of the material prepared in Step A (0.46 g, 0.91 mmol) in 100 mL of acetic acid was placed solid platinum (IV) oxide (200 mg). The mixture was placed under 3 atm hydrogen for 24 h at ambient temperature. The mixture was then filtered through Celite, and concentrated in vacuo. Purification by reverse phase liquid chromatography (25%-65% acetonitrile in water gradient) afforded the title compound as a mixture of cis and trans 1,4-disubstituted cyclohexyl diastereomers. These diastereomers were separated by chiral HPLC (Chiracel OD column, 5% ethanol in hexanes) affording each pure diastereomer: The faster eluting diastereomer: LC/MS 514.4 (M+1); the slower eluting diastereomer: LC/MS 414.4 (M+1-Boc).

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customPurification by reverse phase liquid chromatography (25%-65% acetonitrile in water gradient)

Sources & evidence

ORD record
ord-065ff6981074483db2e5f773a6063930
Source dataset
uspto-grants-2010_03
Patent number
US07671073B2

Reaction notes

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