Sodium Hydroxide → HCID 25183366, compound

HRID 1925710Notes

Reaction equation

HRID 1925710 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C:16]2[CH:20]=[CH:19][S:18][C:17]=2[C:21]([O:23]C)=[O:22])(=[O:14])=[O:13])=[CH:8][CH:7]=1)([CH3:5])[CH2:3][CH3:4].[OH-].[Na+]>CO>[CH3:5][C:2]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C:16]2[CH:20]=[CH:19][S:18][C:17]=2[C:21]([OH:23])=[O:22])(=[O:13])=[O:14])=[CH:8][CH:7]=1)([CH3:1])[CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59180455HCID 59180455, compound

Product 1

HCID 25183366HCID 25183366, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 64 (210 mg; 0.14 mmol) in methanol (2 mL) was added aqueous sodium hydroxide (2 mL; 2N) and the resulting mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure and the resulting residue was dissolved in water, acidified to pH 2 with aqueous hydrochloric acid (2N), and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The desired product was obtained from dichloromethane and hexanes as a yellow solid (75 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe resulting residue was dissolved in water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f020ff7edf034be788a483244b9c8641
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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