Isopropyl iodide → HCID 57845587, compound

HRID 734654Notes

Reaction equation

HRID 734654 reaction equation
N12CCCN=C1CC[CH2:4][CH2:3][CH2:2]2.IC(C)C.[Cl:16][C@H:17]1[C@H:21]([CH2:22][CH2:23][CH2:24][C:25]2[S:29][C:28]([C:30]([OH:32])=[O:31])=[CH:27][CH:26]=2)[C@@H:20]([CH2:33][CH2:34][C:35]2[CH:40]=[C:39]([CH2:41][OH:42])[CH:38]=[C:37]([Cl:43])[CH:36]=2)[C@H:19]([OH:44])[CH2:18]1>CC(C)=O>[Cl:16][C@H:17]1[C@H:21]([CH2:22][CH2:23][CH2:24][C:25]2[S:29][C:28]([C:30]([O:32][CH:3]([CH3:4])[CH3:2])=[O:31])=[CH:27][CH:26]=2)[C@@H:20]([CH2:33][CH2:34][C:35]2[CH:40]=[C:39]([CH2:41][OH:42])[CH:38]=[C:37]([Cl:43])[CH:36]=2)[C@H:19]([OH:44])[CH2:18]1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 24804916HCID 24804916, compound

Product 1

HCID 57845587HCID 57845587, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU, 5.4 μL, 0.036 mmol) and 2-iodopropane (48 μL, 0.48 mmol) were added to a solution of acid 11c (11 mg, 0.024 mmol) in acetone (0.3 mL) at room temperature under nitrogen. After 3 days at room temperature, the reaction mixture was concentrated in vacuo. The residue was acidified with 1.0 N HCl (5 mL) extracted with EtOAc (10 mL). The organic phase was washed with brine (5 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on 3 g silica (10% MeOH/CH2Cl2, gradient) afforded 10 mg (83%) of the title compound (18). 1H NMR (500 MHz, CDCl3) δ□ppm 1.21-1.32 (m, 6 H), 1.32 (s, 3 H), 1.34 (s, 3 H), 1.75-1.80 (m, 6 H), 2.62 (ddd, J=13.91, 9.69, 6.72 Hz, 1 H), 2.71 (td, J=9.35, 5.01 Hz, 1 H), 2.84 (t, J=7.40 Hz, 2 H), 4.03 (q, J=7.09 Hz, 1 H), 4.08-4.18 (m, 1 H), 4.65 (s, 2 H), 5.17 (dt, J=12.47, 6.24 Hz, 1 H), 6.77 (d, J=3.67 Hz, 1 H), 7.08 (d, J=9.54 Hz, 2 H), 7.18 (s, 1 H), 7.60 (d, J=3.67 Hz, 1 H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. extractionextracted with EtOAc (10 mL)
  3. washThe organic phase was washed with brine (5 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash column chromatography on 3 g silica (10% MeOH/CH2Cl2, gradient)

Sources & evidence

ORD record
ord-5c641067bb8642e999e108153486ffef
Source dataset
uspto-grants-2009_09
Patent number
US07592366B2

Reaction notes

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