Isopropyl iodide → HCID 68605268, compound

HRID 218075Notes

Reaction equation

HRID 218075 reaction equation
C1CCN2C(=NCCC2)CC1.I[CH:13]([CH3:15])[CH3:14].[OH:16][C@@H:17]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:18][CH2:19][C@@H:20]([O:29][CH2:30][CH:31]1[CH2:35][CH2:34][C:33](=[O:36])[NH:32]1)[C:21]1[S:25][C:24]([C:26]([OH:28])=[O:27])=[CH:23][CH:22]=1>CC(C)=O>[CH:13]([O:28][C:26]([C:24]1[S:25][C:21]([C@H:20]([O:29][CH2:30][CH:31]2[CH2:35][CH2:34][C:33](=[O:36])[NH:32]2)[CH2:19][CH2:18][C@@H:17]([OH:16])[CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:22][CH:23]=1)=[O:27])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68608006HCID 68608006, compound

Product 1

HCID 68605268HCID 68605268, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

DBU (9 μL, 0.06 mmol) and 2-iodopropane (62 μL, 0.62 mmol) were added to a solution of acid 6 (12 mg, 0.031 mmol) in acetone (0.3 mL) at room temperature under nitrogen. After 5 days at room temperature, the solvent was removed under a stream of nitrogen. The residue was acidified with 1 N HCl (2 mL) and extracted with EtOAc (3×10 mL). The combined extracts were washed with brine (5 mL) then dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica (CH2Cl2→10% MeOH/CH2Cl2) afforded 11.3 mg (85%) of the title compound.

Workup

  1. customthe solvent was removed under a stream of nitrogen
  2. extractionextracted with EtOAc (3×10 mL)
  3. washThe combined extracts were washed with brine (5 mL)
  4. dry with materialthen dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash column chromatography on silica (CH2Cl2→10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2ef0fe04003c4bd4b47fed366aee5965
Source dataset
uspto-grants-2012_06
Patent number
US08198315B2

Reaction notes

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