Water → HCID 67305878, compound

HRID 17853Notes

Reaction equation

HRID 17853 reaction equation
[CH:1]1([N:4]2[C:9]3[CH:10]=[CH:11][C:12]([O:14]C)=[CH:13][C:8]=3[S:7](=[O:17])(=[O:16])[NH:6][CH2:5]2)[CH2:3][CH2:2]1.B(Br)(Br)Br.O>C(Cl)(Cl)Cl>[CH:1]1([N:4]2[C:9]3[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:8]=3[S:7](=[O:16])(=[O:17])[NH:6][CH2:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 67307374HCID 67307374, compound

Product 1

HCID 67305878HCID 67305878, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of the compound of Example 84 (50 mg) in chloroform (3 mL) is cooled on an ice bath and then boron tribromide (0.15 mL) is added. After stirring for 20 hours, water (5 mL) is added to the mixture, which is then concentrated under reduced pressure and subsequently extracted with ethyl acetate (3×20 mL). The organic phases are collected and dried over anhydrous MgSO4. After filtration, the filtrate is evaporated to dryness and the residue is dissolved in ethyl acetate (1 mL); hexane (5 mL) is then added. The precipitate obtained is collected by filtration, washed with hexane and dried to yield the expected product in the form of a white solid.

Workup

  1. concentrationis then concentrated under reduced pressure
  2. extractionsubsequently extracted with ethyl acetate (3×20 mL)
  3. customThe organic phases are collected
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationAfter filtration
  6. customthe filtrate is evaporated to dryness
  7. dissolutionthe residue is dissolved in ethyl acetate (1 mL)
  8. additionhexane (5 mL) is then added
  9. customThe precipitate obtained
  10. filtrationis collected by filtration
  11. washwashed with hexane
  12. customdried

Sources & evidence

ORD record
ord-3bd330c5b3bc4af1bd2bc4b371ae63d6
Source dataset
uspto-grants-2010_06
Patent number
US07741320B2

Reaction notes

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