Hydrochloric Acid → HCID 24694245, compound

HRID 709592Notes

Reaction equation

HRID 709592 reaction equation
C[O:2][C:3](=[O:13])[CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][N:7]=1.O[Li].O.Cl>C1COCC1.O>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([S:5][CH2:4][C:3]([OH:13])=[O:2])=[N:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 60735499HCID 60735499, compound

Product 1

HCID 24694245HCID 24694245, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the solution of the ester 14 (0.43 g, 2.0 mmol) in THF (18 mL) was added LiOH.H2O (0.17 g, 4 mmol) as a solution in 5 mL of H2O. The reaction mixture was stirred at room temperature and monitored by TLC. When no staring material was observed, the reaction mixture was acidified with 1N HCl, (˜4.5 mL) and concentrated under reduce pressure to remove the organic solvent. The mixture was diluted with 15 mL of H2O and extracted with EtOAc (2×120 mL). The organic layer was washed with brine, dried over Na2SO4, concentrated and dried under high vacuum over P2O5 to give 0.40 g (98% yield) of compound 15 which was used in subsequent reaction without further purification.

Workup

  1. concentrationconcentrated
  2. customto remove the organic solvent
  3. additionThe mixture was diluted with 15 mL of H2O
  4. extractionextracted with EtOAc (2×120 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. dry with materialdried under high vacuum over P2O5

Sources & evidence

ORD record
ord-2066320b56bc470c9b149d6a52ef7c14
Source dataset
uspto-grants-2015_11
Patent number
US09181219B2

Reaction notes

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