Isopropyl iodide → HCID 53241572, compound

HRID 734623Notes

Reaction equation

HRID 734623 reaction equation
[CH2:1]1[CH2:11]CN2C(=NCCC2)C[CH2:2]1.[OH:12][CH:13]([C:19]1[CH:24]=[CH:23][C:22]([N:25]2[C:29](=[O:30])[CH2:28][CH2:27][C@@H:26]2[CH2:31][CH2:32][CH2:33][C:34]2[S:38][C:37]([C:39]([OH:41])=[O:40])=[CH:36][CH:35]=2)=[CH:21][CH:20]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].IC(C)C>CC(C)=O>[CH:1]([O:40][C:39]([C:37]1[S:38][C:34]([CH2:33][CH2:32][CH2:31][C@H:26]2[CH2:27][CH2:28][C:29](=[O:30])[N:25]2[C:22]2[CH:21]=[CH:20][C:19]([CH:13]([OH:12])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:24][CH:23]=2)=[CH:35][CH:36]=1)=[O:41])([CH3:11])[CH3:2]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11855868HCID 11855868, compound

Product 1

HCID 53241572HCID 53241572, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

DBU (5.2 μL, 0.035 mmol) was added to a solution of acid 43 (7.5 mg, 0.017 mmol) in acetone (0.1 mL) at rt under nitrogen. After 10 min, 2-iodopropane (35 μL, 0.35 mmol) was added. After 21 h at rt, the reaction was quenched with 0.01 N HCl (3 mL) and extracted with EtOAc (3×4 mL). The combined extracts were washed with brine (5 mL), dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica (CH2Cl2→1% MeOH/CH2Cl2) afforded 4.6 mg (53%) of the title compound (44).

Workup

  1. waitAfter 21 h at rt
  2. customthe reaction was quenched with 0.01 N HCl (3 mL)
  3. extractionextracted with EtOAc (3×4 mL)
  4. washThe combined extracts were washed with brine (5 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash column chromatography on silica (CH2Cl2→1% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-398303fe4b03401a9e93983986ffae85
Source dataset
uspto-grants-2009_09
Patent number
US07592364B2

Reaction notes

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