Citric Acid → HCID 8707028, compound

HRID 401655Notes

Reaction equation

HRID 401655 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-81ac9dcf50184e33a57dcfaef337e3ce
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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