Hydrochloric Acid → HCID 11245248, compound

HRID 855031Notes

Reaction equation

HRID 855031 reaction equation
[Cl:1][C:2]1[C:11]([O:12][CH2:13][CH3:14])=[C:10]([Cl:15])[CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:20]([O:22]CC)=[O:21])[CH:6]([C:16]([F:19])([F:18])[F:17])[O:7]2.O.[OH-].[Li+].Cl>C1COCC1.C(O)C.O>[Cl:1][C:2]1[C:11]([O:12][CH2:13][CH3:14])=[C:10]([Cl:15])[CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:20]([OH:22])=[O:21])[CH:6]([C:16]([F:18])([F:19])[F:17])[O:7]2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 69526566HCID 69526566, compound

Product 1

HCID 11245248HCID 11245248, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

The product of step 1 was dissolved in 5 mL THF and 1 mL ethanol. A solution of 61 mg of lithium hydroxide monohydrate in 6 mL of water was added to the organic solution. The vessel was capped and heated to 80° C. for 1 hour. After cooling to room temperature, the sample was concd using a nitrogen stream. The basic solution was then acidified with 3N HCl until the pH=2 and extracted 4 times with ethyl acetate. The organic layers were combined, dried over sodium sulfate, filtered and solvent removed. The sample was purified by reverse phase chromatography to afford 72.6 mg (70%) of a brown solid: 1H NMR (CDCl3, CD3OD/300 MHz) 1.46 (t, 3H, J=6.6 Hz), 4.08 (q, 2H, J=7.2 Hz), 5.71 (q, 2H, J=6.9 Hz), 7.01 (s, 1H), 8.08 (s, 1H); MS (ES+) 357 (M+1, 100), 359 (M+3, 68); LC-MS purity 100% at 3.166 min. (UV and ELSD); HRMS (ES−) m/z calcd for (M−1; C13H8O4Cl2F3) 354.9746, found 354.9744.

Workup

  1. customThe vessel was capped
  2. temperatureAfter cooling to room temperature
  3. extractionextracted 4 times with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customsolvent removed
  7. customThe sample was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-46ccac310ef34109aa733c6052c0fcc5
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

Loading…