Citric Acid → HCID 8707028, compound

HRID 2365628Notes

Reaction equation

HRID 2365628 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][C:8]=1[Cl:17].[Li+].[OH-].C1COCC1.CO.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[Cl:17]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 21892291Methanol tetrahydrofuran waterHCID 44570905HCID 44570905, compound

Product 1

HCID 8707028HCID 8707028, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of compound 27c (662 mg, 2.0 mmol) and LiOH (192 mg, 8 mmol) in a solvent mixture of THF/MeOH/H2O (3/3/3 mL) was stirred at room temperature for 4 h, then acidified with 15% citric acid in H2O. The mixture was extracted with EtOAc (3×), and the combined extracts washed sequentially with water and brine. The extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The resultant crude compound 3b was dried under reduced pressure for 18 h and used in the following reaction without further purification.

Workup

  1. extractionThe mixture was extracted with EtOAc (3×)
  2. washthe combined extracts washed sequentially with water and brine
  3. dry with materialThe extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dry with materialThe resultant crude compound 3b was dried under reduced pressure for 18 h
  7. customused in the following reaction without further purification

Sources & evidence

ORD record
ord-4ee91feae0744b27865e6e8bb3fb9a40
Source dataset
uspto-grants-2014_04
Patent number
US08697683B2

Reaction notes

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