Pyridine → HCID 16749201, compound

HRID 1350213Notes

Reaction equation

HRID 1350213 reaction equation
[NH2:1]/[C:2](=[N:13]\[O:14][C:15]([C@H:17]([CH2:26][CH2:27][CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=O)/[CH:3]1[CH2:8][CH2:7][N:6]([S:9]([CH3:12])(=[O:11])=[O:10])[CH2:5][CH2:4]1.N1C=CC=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O.[Cl-].[Cl-].[Zn+2]>[CH:29]1([CH2:28][CH2:27][CH2:26][C@@H:17]([C:15]2[O:14][N:13]=[C:2]([CH:3]3[CH2:8][CH2:7][N:6]([S:9]([CH3:12])(=[O:11])=[O:10])[CH2:5][CH2:4]3)[N:1]=2)[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

6

Reactant 2

HCID 1049PyridineHCID 16749428HCID 16749428, compound

Product 1

HCID 16749201HCID 16749201, compoundYield 36.2%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl(3R)-3-{[({(Z)-amino[1-(methylsulfonyl)-4-piperidinyl]methylidene}amino)oxy]carbonyl}-6-cyclohexylhexanoate (preparation 42) (1.50 g, 1.83 mmol) in toluene (100 ml) was treated with pyridine (90 μl, 1.83 mmol) and anhydrous ZnCl2 (150 mg, 1.83 mmol) and heated at reflux for 20 hours. The reaction mixture was diluted with EtOAc and washed with H2O, brine and H2O, dried over anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure. The residue was purified on a silica column eluting with a solvent gradient of cyclohexane:EtOAc (90:10) gradually changing to (50:50). The oil was recrystallised from pentane to afford the title compound as a white solid (320 mg, 36%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 20 hours
  3. washwashed with H2O, brine and H2O
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified on a silica column
  8. washeluting with a solvent gradient of cyclohexane:EtOAc (90:10)
  9. customThe oil was recrystallised from pentane

Sources & evidence

ORD record
ord-43f0e0fc008c4957afcbb0c8bad4fb2b
Source dataset
uspto-grants-2007_05
Patent number
US07214694B2

Reaction notes

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