Ethanol → HCID 58934496, compound

HRID 855021Notes

Reaction equation

HRID 855021 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([S:20][CH3:21])[N:15]=1)[O:9][CH:8]([C:22]([F:25])([F:24])[F:23])[C:7]([C:26]([O:28]CC)=[O:27])=[CH:6]2)[CH3:2].[OH-].[Li+].C(O)C>O1CCCC1.O>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([S:20][CH3:21])[N:15]=1)[O:9][CH:8]([C:22]([F:25])([F:24])[F:23])[C:7]([C:26]([OH:28])=[O:27])=[CH:6]2)[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 69518541HCID 69518541, compound

Product 1

HCID 58934496HCID 58934496, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 100 mg (0.23 mmol) intermediate isolated from step 2 in 1.5 mL of tetrahydrofuran was added a solution of 48 mg (1.2 mmol) lithium hydroxide in 2.5 mL of water, followed by addition of 2.5 mL of ethanol. The reaction was then heated to reflux for one h. After cooling to room temperature, the volatiles were removed, the residue was diluted with water, then acidified at 0° C. with dilute hydrochloric acid to pH=1.0. The product was extracted with ethyl ether. The combined organic phases were washed with brine, dried over anhydrous magnesium sulfate and concd in vacuo to afford 50 mg (53%) of a yellow solid: 1H NMR (CDCl3/400 MHz) 8.40(d, J=6 Hz, 1H), 7.85(s, 1H), 7.17(s, 1H), 6.78(s, 1H, 6.58(d, J=5.6 Hz, 1H), 5.66(q, J=7.2 Hz, 1H), 2.48(q, J=7.2 Hz, 2H), 2.29(s, 3H), 1.l4(t, J=7.6 Hz, 3H); MS (ES+) 413 (M+l, 100), HRMS (EI) m/z calcd for (C18H16F3N2O4S) 413.0777, found 413.0768.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux for one h
  3. customthe volatiles were removed
  4. additionthe residue was diluted with water
  5. customacidified at 0° C. with dilute hydrochloric acid to pH=1.0
  6. extractionThe product was extracted with ethyl ether
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate and concd in vacuo

Sources & evidence

ORD record
ord-d4cc9c052c6f4adaa6ce2dea917f7638
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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