Hydrochloric Acid → HCID 61395640, compound

HRID 2358764Notes

Reaction equation

HRID 2358764 reaction equation
C([O:3][C:4](=[O:22])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[N+:19]([O-:21])=[O:20])[CH:6]=1)C.C1COCC1.O.O.[OH-].[Li+].Cl>O>[F:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:4]([OH:22])=[O:3])=[C:13]([N+:19]([O-:21])=[O:20])[CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 21881883Oxolane--water (1/1)HCID 52466667HCID 52466667, compound

Product 1

HCID 61395640HCID 61395640, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The product from Example 181a (3.0 g, 9.8 mmol) was added to a solution of THF/H2O (5:1). Lithium hydroxide monohydrate (0.82 g, 19.5 mmol) was added in one portion. The solution was warmed to 60° C. for 2 h. The reaction was cooled. Distilled water was added. The pH was adjusted to 4.0 with 10% HCl. The mixture was extracted with ethyl acetate. The combined organic phases were washed with water, saturated NaHCO3, water, brine, and dried over sodium sulfate, filtered and concentrated under vacuum giving the title compound (2.65 g, 97%).

Workup

  1. temperatureThe reaction was cooled
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe combined organic phases were washed with water, saturated NaHCO3, water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1864c442cfa2431fb3b49ca2c9b39d13
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

Loading…