Bicarbonate Ion → HCID 67007739, compound

HRID 1946599Notes

Reaction equation

HRID 1946599 reaction equation
Cl.Cl.[CH2:3]([N:10]1[CH2:15][CH:14]2[CH2:16][CH:11]1[CH2:12][NH:13]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.F[C:18]1[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=1.C(=O)(O)[O-]>CS(C)=O>[CH2:3]([N:10]1[CH2:15][C@H:14]2[CH2:16][C@@H:11]1[CH2:12][N:13]2[C:18]1[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 769Bicarbonate IonHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 67007853HCID 67007853, compound

Product 1

HCID 67007739HCID 67007739, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A stirring solution of title compound 206 (0.5 g, 1.914 mmol) and ethyl 4-fluorobenzoate (0.421 ml, 2.87 mmol) in DMSO (19.14 mL) was stirred at 140° C. overnight. The mixture was cooled down and poured over a diluted aqueous solution of bicarbonate and extracted with ethyl acetate (twice). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated. The crude was purified by flash chromatography: 0% to 60% ethyl acetate in hexanes over 20 min on 20 g SiO2 to afford title compound 207 (0.33 g, 51%) as beige oil. LRMS: (calc) 336.18 (found) 337.4 (MH)+.

Workup

  1. temperatureThe mixture was cooled down
  2. extractionextracted with ethyl acetate (twice)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-d23eb5f64771451a84731008554c3595
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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