HCID 86697920, compound → HCID 86697922, compound

HRID 338106Notes

Reaction equation

HRID 338106 reaction equation
[CH2:1]([N:4]1[CH2:11][CH:10]2[C:6]([C:23]3[S:24][C:25]([F:28])=[CH:26][CH:27]=3)([N:7]([C:12]([NH:14][C:15](=[O:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[S:13])[O:8][CH2:9]2)[CH2:5]1)[CH:2]=[CH2:3]>[Zn].C(O)(=O)C>[CH2:1]([N:4]1[CH2:11][CH:10]([CH2:9][OH:8])[C:6]([NH:7][C:12]([NH:14][C:15](=[O:22])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[S:13])([C:23]2[S:24][C:25]([F:28])=[CH:26][CH:27]=2)[CH2:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 1

HCID 86697920HCID 86697920, compound

Product 1

HCID 86697922HCID 86697922, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To N-[5-allyl-6a-(5-fluoro-2-thienyl)-3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-1-carbothioyl]benzamide (6.91 g, 16.5 mmol) is added acetic acid (110 mL) followed by powdered zinc (10.8 g). The resulting gray mixture is rapidly stirred at room temperature for 40 minutes. The mixture is filtered through diatomaceous earth while rinsing with methanol (approximately 250 mL). The filtrate is concentrated under reduced pressure, diluted with methanol (200 mL), and concentrated under reduced pressure. The residue is dissolved in dichloromethane (300 mL) and treated with 1 M potassium carbonate solution (200 mL). The resulting emulsion is filtered through diatomaceous earth while rinsing with water (approximately 40 mL) and dichloromethane (200 mL). The phases are separated and the aqueous phase is further extracted with dichloromethane (100 mL). The combined dichloromethane extracts are dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (6.65 g, 96%). ES/MS (m/e): 420 (M+H).

Workup

  1. filtrationThe mixture is filtered through diatomaceous earth
  2. washwhile rinsing with methanol (approximately 250 mL)
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. additiondiluted with methanol (200 mL)
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue is dissolved in dichloromethane (300 mL)
  7. additiontreated with 1 M potassium carbonate solution (200 mL)
  8. filtrationThe resulting emulsion is filtered through diatomaceous earth
  9. washwhile rinsing with water (approximately 40 mL) and dichloromethane (200 mL)
  10. customThe phases are separated
  11. extractionthe aqueous phase is further extracted with dichloromethane (100 mL)
  12. dry with materialThe combined dichloromethane extracts are dried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3851767a905a4a619deb8e5419bc6356
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

Loading…