Potassium Carbonate → HCID 89954796, compound

HRID 705367Notes

Reaction equation

HRID 705367 reaction equation
[CH:1]1([C:4]2[C:9]([N:10]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[S:11]([CH3:14])(=[O:13])=[O:12])=[CH:8][N:7]3[NH:20][C:21]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)=[C:22]([C:23]([O:25][CH3:26])=[O:24])[CH:6]3[CH:5]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CS(C)=O.C(OCC)(=O)C>[CH:1]1([C:4]2[C:9]([N:10]([CH2:15][CH2:16][CH:17]([CH3:18])[CH3:19])[S:11]([CH3:14])(=[O:13])=[O:12])=[CH:8][N:7]3[N:20]=[C:21]([C:27]4[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=4)[C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:6]3[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12217721Iodo benzene diacetateHCID 89955387HCID 89955387, compound

Product 1

HCID 89954796HCID 89954796, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 17K in dimethyl sulfoxide (8 mL) was treated with potassium carbonate (237 mg, 1.71 mmol) and iodobenzene diacetate (552 mg, 1.71 mmol) followed by stirring for 1 hour. The mixture was diluted with ethyl acetate and the organic layer was washed with water and saturated sodium chloride solution, dried (Na2SO4), filtered and concentrated in vacuo to afford a brown oil. Purification by chromatography on a 100 g silica gel cartridge, eluting with 15-80% ethyl acetate in hexanes, afforded the title compound as a rigid foam (166 mg, 23% over two steps). 1H NMR (500 MHz, CDCl3) δ ppm 8.48 (s, 1H), 7.75 (m, 2H), 7.67 (s, 1H), 7.15 (m, 2H), 3.82 (s, 3H), 3.68 (m, 1H), 3.64 (m, 1H), 3.07 (s, 3H), 2.29 (m, 1H), 1.62 (m, 1H), 1.51 (m, 1H), 1.23 (m, 2H), 1.07 (m, 1H), 0.94 (m, 6H), 0.82 (m, 1H); MS (ESI+) m/z 474 (M+H)+.

Workup

  1. washthe organic layer was washed with water and saturated sodium chloride solution
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto afford a brown oil
  6. customPurification by chromatography on a 100 g silica gel cartridge
  7. washeluting with 15-80% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-76ff9f129407471098fc0c92617e2742
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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