Potassium sodium tartarate → HCID 67396163, compound

HRID 714665Notes

Reaction equation

HRID 714665 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[C:12]([C:14](OC)=[O:15])[CH:11]=[C:10]([C:18]([O:20][CH3:21])=[O:19])[CH:9]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[C:10]([C:18]([O:20][CH3:21])=[O:19])[CH:9]=1

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 67396591HCID 67396591, compound

Product 1

HCID 67396163HCID 67396163, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

305 mg (1.00 mmol) of the compound from Example 110A were dissolved in 6 ml of THF, and 0.5 ml (0.50 mmol) of a 1 M solution of lithium aluminum hydride in THF was added at −10° C. The reaction mixture was then stirred at RT for 1 h. For work-up, 3 ml of saturated aqueous sodium potassium tartrate solution were added at RT, and the mixture was extracted with 15 ml of ethyl acetate. The organic phase was washed once with 10 ml of saturated sodium potassium tartrate solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified chromatographically [Method 19]. This gave 189 mg (68% of theory) of the target compound.

Workup

  1. extractionthe mixture was extracted with 15 ml of ethyl acetate
  2. washThe organic phase was washed once with 10 ml of saturated sodium potassium tartrate solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-338db8e8a4bc4954bb00267b476f00e9
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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