Potassium sodium tartarate → HCID 67056312, compound

HRID 714645Notes

Reaction equation

HRID 714645 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][N:18]=1)[C:12](OC)=[O:13].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[F:19][C:2]([F:1])([F:20])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]([CH2:12][OH:13])[CH:16]=[CH:17][N:18]=1

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 67396524HCID 67396524, compound

Product 1

HCID 67056312HCID 67056312, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

432 mg (1.54 mmol) of the compound from Example 58A were dissolved in 10 ml of THF, and 1.08 ml (1.08 mmol) of a 1 M solution of lithium aluminum hydride in THF were added at −10° C. After the addition had ended, the mixture was stirred at RT for 2 h. For work-up, 4 ml of a saturated 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. This gave 497 mg (>100% of theory) of the target compound which were reacted further without any further purification.

Workup

  1. additionAfter the addition
  2. extractionthe mixture was extracted with 15 ml of ethyl acetate
  3. washThe organic phase was washed once with 10 ml of saturated sodium potassium tartrate solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThis gave 497 mg (>100% of theory) of the target compound which were reacted further without any further purification

Sources & evidence

ORD record
ord-415161255ab148c5b224d675d6e329b8
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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