Isopropyl iodide → HCID 68973796, compound

HRID 657571Notes

Reaction equation

HRID 657571 reaction equation
[C:1]([O:5][C:6](=[O:37])[N:7]([CH2:18][CH2:19][C:20]([N:22]1[CH2:28][CH2:27][C:26]2[CH:29]=[C:30]([O:35][CH3:36])[C:31]([O:33][CH3:34])=[CH:32][C:25]=2[CH2:24][CH2:23]1)=[O:21])[CH2:8][CH:9]1[CH2:16][C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([OH:17])[CH:14]=2)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].[CH:50](I)([CH3:52])[CH3:51]>CN(C=O)C.O>[C:1]([O:5][C:6](=[O:37])[N:7]([CH2:18][CH2:19][C:20]([N:22]1[CH2:23][CH2:24][C:25]2[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[CH:29][C:26]=2[CH2:27][CH2:28]1)=[O:21])[CH2:8][CH:9]1[CH2:16][C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([O:17][CH:50]([CH3:52])[CH3:51])[CH:14]=2)([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 68973802HCID 68973802, compound

Product 1

HCID 68973796HCID 68973796, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.4 g (2.7 mmoles) of the product of Step 1 are dissolved in 15 mL of DMF. There are then added 740 mg (2 equivalents) of potassium carbonate, 160 mg (0.18 equivalent) of caesium carbonate and 0.54 mL (2 equivalents) of isopropyl iodide. Heating is then carried out at 40° C. for 24 hours. The DMF is evaporated off using a rotary evaporator. The residue obtained is then diluted with water and extracted with CH2Cl2. The organic phase is then dried over MgSO4, filtered and evaporated to dryness. An oil is obtained which is purified by flash chromatography over 100 g of silica (eluant: CH2Cl2/ethyl acetate: 80/20) to yield the expected product in the form of a sticky meringue.

Workup

  1. temperatureHeating
  2. customThe DMF is evaporated off
  3. customa rotary evaporator
  4. customThe residue obtained
  5. extractionextracted with CH2Cl2
  6. dry with materialThe organic phase is then dried over MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customAn oil is obtained which
  10. customis purified by flash chromatography over 100 g of silica (eluant: CH2Cl2/ethyl acetate: 80/20)

Sources & evidence

ORD record
ord-bf3986efed9242cc948e3a0291c0eabd
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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