Isopropyl iodide → HCID 11316917, compound

HRID 349351Notes

Reaction equation

HRID 349351 reaction equation
N12CCCN=C1CC[CH2:4][CH2:3][CH2:2]2.[Cl:12][C:13]1[CH:14]=[C:15]([CH2:19][CH:20]([OH:39])/[CH:21]=[CH:22]/[C@H:23]2[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[N:24]2[CH2:30][CH2:31][CH2:32][CH2:33][O:34][CH2:35][C:36]([OH:38])=[O:37])[CH:16]=[CH:17][CH:18]=1.IC(C)C>CC(C)=O>[CH:3]([O:37][C:36](=[O:38])[CH2:35][O:34][CH2:33][CH2:32][CH2:31][CH2:30][N:24]1[C:25](=[O:29])[CH2:26][CH2:27][CH2:28][C@@H:23]1/[CH:22]=[CH:21]/[CH:20]([OH:39])[CH2:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([Cl:12])[CH:14]=1)([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11327328HCID 11327328, compound

Product 1

HCID 11316917HCID 11316917, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU, 16 μL, 0.11 mmol) was added to a solution of (4-{(R)-2-[(E)-4-(3-chlorophenyl)-3-hydroxy-but-1-enyl]-6-oxo-piperidin-1-yl}-butoxy)-acetic acid (29 mg, 0.071 mmol) in acetone (0.5 mL). After 5 min, 2-iodopropane (35 μL, 0.35 mmol) was added. After 17 h, the reaction mixture was concentrated in vacuo, EtOAc (15 mL) was added and the resultant mixture was washed with 0.5 M aqueous HCl (5 mL), saturated aqueous NaHCO3 (5 mL) and brine (5 mL). The organic phase was then dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (CH2Cl2→5% MeOH/CH2Cl2, gradient) afforded 16 mg (50%) of the title compound.

Workup

  1. waitAfter 17 h
  2. concentrationthe reaction mixture was concentrated in vacuo, EtOAc (15 mL)
  3. additionwas added
  4. washthe resultant mixture was washed with 0.5 M aqueous HCl (5 mL), saturated aqueous NaHCO3 (5 mL) and brine (5 mL)
  5. dry with materialThe organic phase was then dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash column chromatography on silica gel (CH2Cl2→5% MeOH/CH2Cl2, gradient)

Sources & evidence

ORD record
ord-15a85b93f8a54a96ab735c09bad0f40e
Source dataset
uspto-grants-2007_02
Patent number
US07179820B2

Reaction notes

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