Sodium Hydroxide → HCID 16060158, compound

HRID 714638Notes

Reaction equation

HRID 714638 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[S:12][C:11]([C:13]([O:15]C)=[O:14])=[CH:10][CH:9]=1.[OH-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[S:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 5098321HCID 5098321, compound

Product 1

HCID 16060158HCID 16060158, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

289 mg (1.14 mmol) of the compound from Example 46A were dissolved in 2 ml of THF/methanol (1:1), and 1.14 ml (2.29 mmol) of 2 M aqueous sodium hydroxide solution were added. The reaction mixture was stirred at 80° C. for 2 h. After cooling to RT, the solvent was removed on a rotary evaporator and the residue was taken up in 5 ml of water and washed with 5 ml of ethyl acetate. The aqueous phase was acidified with 1 N hydrochloric acid and extracted twice with in each case 5 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. This gave, in a purity of 91%, 218 mg (73% of theory) of the target compound.

Workup

  1. temperatureAfter cooling to RT
  2. customthe solvent was removed on a rotary evaporator
  3. washwashed with 5 ml of ethyl acetate
  4. extractionextracted twice with in each case 5 ml of ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-37ad06b03fe349ac975b1684122791c7
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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