Hydrochloric Acid → HCID 25183370, compound

HRID 1925678Notes

Reaction equation

HRID 1925678 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:20]([O:22]C)=[O:21])(=[O:13])=[O:12])=[C:7]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl>O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:20]([OH:22])=[O:21])(=[O:12])=[O:13])=[C:7]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59180453HCID 59180453, compound

Product 1

HCID 25183370HCID 25183370, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 11 (24.7 mL; 0.06 mmol) in tetrahydrofuran (5 mL) in a 2.5-5.0 mL microwave reactor tube was added aqueous lithium hydroxide (1 mL; 2M). The reaction vessel was subjected to the following microwave conditions: Temperature=140° C.; Time=15 minutes; Power=250 W; Cooling on; Absorption=Very High. The crude reaction mixture was allowed to cool to room temperature, acidified by the addition of aqueous hydrochloric acid (15 mL; 2N), and extracted with ethyl acetate (3×10 mL). The organic phases were combined and dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford a beige solid. The latter was triturated from diisopropyl ether to yield the title compound as a beige solid (24.1 mg).

Workup

  1. customTemperature=140° C.
  2. customTime=15 minutes
  3. temperatureCooling on
  4. customAbsorption=Very High
  5. customThe crude reaction mixture
  6. extractionextracted with ethyl acetate (3×10 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto afford a beige solid
  11. customThe latter was triturated from diisopropyl ether

Sources & evidence

ORD record
ord-416cabbc037f4ba3baf4ae5b5f4f87ee
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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