Potassium Carbonate → HCID 18791995, compound

HRID 1005542Notes

Reaction equation

HRID 1005542 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][O:16][CH2:17][CH2:18][O:19][C:20](=[O:26])[CH2:21][CH2:22][C:23]([O-:25])=[O:24])[C:13]([CH3:27])=[N:12][C:11]=2[CH:28]([CH3:30])[CH3:29])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:37]([O:43][CH2:44]I)(=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39]>CN(C)C=O>[C:20]([O:19][CH2:18][CH2:17][O:16][CH2:15][N:14]1[C:10]([S:9][C:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[CH:3]=2)=[C:11]([CH:28]([CH3:30])[CH3:29])[N:12]=[C:13]1[CH3:27])(=[O:26])[CH2:21][CH2:22][C:23]([O:25][CH2:44][O:43][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])=[O:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 104401Iodomethyl pivalateHCID 86755352HCID 86755352, compound

Product 1

HCID 18791995HCID 18791995, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of the compound 68 (100 mg, 0.230 mmol) and potassium carbonate (48.0 mg, 0.345 mmol) in N,N-dimethylformamide (1 mL) was added pivaloyloxymethyl iodide (61 mg, 0.252 mmol), and stirred at room temperature for 2 hours. The reaction mixture was partitioned between ice-water and ethyl acetate - hexane (1:1)). The organic layer was separated, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluate: hexane - ethyl acetate (1:1)) to give the compound 74 (111 mg, 88%) as pale yellow oil. Rf 0.15 (1:1 EtOAc-hexane).

Workup

  1. customThe reaction mixture was partitioned between ice-water and ethyl acetate - hexane (1:1))
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on a silica gel column (eluate: hexane - ethyl acetate (1:1))

Sources & evidence

ORD record
ord-4fc427bb1ad74e6bb731d52e61f0bea8
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Reaction notes

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