Sodium Hydroxide → HCID 25183506, compound

HRID 1925754Notes

Reaction equation

HRID 1925754 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([S:15]([NH:18][C:19]2[CH:23]=[CH:22][S:21][C:20]=2[C:24]([O:26]C)=[O:25])(=[O:17])=[O:16])[CH:10]=1.[OH-].[Na+]>O1CCCC1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([S:15]([NH:18][C:19]2[CH:23]=[CH:22][S:21][C:20]=2[C:24]([OH:26])=[O:25])(=[O:17])=[O:16])[CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67520705HCID 67520705, compound

Product 1

HCID 25183506HCID 25183506, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 154 (172 mg; 0.43 mmol) in tetrahydrofuran (2.1 mL) was placed in a 2.5-5.0 mL microwave reactor tube. Aqueous sodium hydroxide (2.1 mL; 2N) was added and the reaction vessel was subjected to the following microwave conditions: Temperature=140° C.; Time=30 minutes; Power=250 W; Cooling on; Absorption=High. After cooling to room temperature, the reaction mixture was acidified with aqueous hydrochloric acid (25 mL; 6N) and extracted with ethyl acetate (40 mL×2). The organic layers were combined and successively washed with aqueous sodium hydroxide (20 mL; 2N), aqueous hydrochloric acid (25 mL; 6N), and aqueous saturated sodium chloride (25 mL). The dichloromethane extracts were dried over magnesium sulfate, filtered, and concentrated under reduced. The resulting white solid was purified by silica gel chromatography (2 columns; 1st column gradient: 16% ethyl acetate in hexanes to 5% methanol in dichloromethane; 2nd column gradient: dichloromethane to 5% methanol in dichloromethane) to yield the title compound as a white solid (61 mg).

Workup

  1. customTemperature=140° C.
  2. customTime=30 minutes
  3. temperatureCooling on
  4. customAbsorption=High
  5. extractionextracted with ethyl acetate (40 mL×2)
  6. washsuccessively washed with aqueous sodium hydroxide (20 mL; 2N), aqueous hydrochloric acid (25 mL; 6N), and aqueous saturated sodium chloride (25 mL)
  7. dry with materialThe dichloromethane extracts were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting white solid was purified by silica gel chromatography (2 columns; 1st column gradient: 16% ethyl acetate in hexanes to 5% methanol in dichloromethane; 2nd column gradient: dichloromethane to 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-670c867a6359483aa249af854ec4ed5b
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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