Hydrochloric Acid → HCID 67147487, compound

HRID 2426989Notes

Reaction equation

HRID 2426989 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17]([O:19]C)=[O:18])[CH:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.[Li+].[OH-].Cl>C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17]([OH:19])=[O:18])[CH:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67147503HCID 67147503, compound

Product 1

HCID 67147487HCID 67147487, compoundYield 105.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of the product of Step 1 (0.1 g) and LiOH (3 mL, 1N) in 15 mL of 1:1:1 THF/MeOH/H2O was stirred for two days at room temperature and heated at 55° C. for 20 h. The mixture was cooled and treated with 5 mL of 1N HCl, followed by extraction with 30 mL of EtOAc. The EtOAc extract was dried over Na2SO4, filtered and concentrated to give the crude product (0.1 g) which was used for next step without further purification.

Workup

  1. temperatureheated at 55° C. for 20 h
  2. temperatureThe mixture was cooled
  3. extractionfollowed by extraction with 30 mL of EtOAc
  4. extractionThe EtOAc extract
  5. dry with materialwas dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-69c304f2265d48998af562e3daf6e133
Source dataset
uspto-grants-2011_06
Patent number
US07968578B2

Reaction notes

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