Isopropyl iodide → HCID 178460294, compound

HRID 1355602Notes

Reaction equation

HRID 1355602 reaction equation
[OH:1][NH:2][C:3]([C:5]1[C:6]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[N:7][C:8]([CH2:11][NH2:12])=[CH:9][CH:10]=1)=[NH:4].I[CH:21]([CH3:23])[CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+].C(OC(=O)C)C.CCCCCC>CN(C)C=O.C(OC(=O)C)C>[CH:21]([O:1][NH:2][C:3]([C:5]1[C:6]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[N:7][C:8]([CH2:11][NH2:12])=[CH:9][CH:10]=1)=[NH:4])([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 21226206Ethyl acetate hexaneHCID 178450826HCID 178450826, compound

Product 1

HCID 178460294HCID 178460294, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of the product of Example 54 (11-6) (0.43 g, 1.39 mmol) in dimethylformamide (5 ml) was added 2-iodopropane (210 μl, 2.1 mmol), followed by cesium carbonate (0.68 g, 2.1 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethylacetate and washed with sodium bicarbonate (saturated). The organic layer was dried over sodium sulfate, filtered and concentrated to give an orangish oil. Flash column chromatography performed in 1/1 ethylacetate/hexane followed by ethylacetate yielded 229 mg (53%) product as a crystalline solid. NMR δ (ppm) CDCl3: 8.8 (d, 1H), 7.9 (dd, 1H), 7.3 (d, 1H), 5.5 (bs, 1H), 4.7 (bs, 2H), 4.4 (d, 1H), 1.4 (s, 9H), 1.3 (d, 6H).

Workup

  1. washwashed with sodium bicarbonate (saturated)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give an orangish oil

Sources & evidence

ORD record
ord-15822fe9c6be4e6593d599427db1a2a6
Source dataset
uspto-grants-2003_07
Patent number
US06586405B2

Reaction notes

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