N-bromobutanimide → HCID 10202424, compound

HRID 478315Notes

Reaction equation

HRID 478315 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]([C:15]([O:17]CC)=[O:16])=[C:13]([CH2:20][CH2:21][CH2:22][CH3:23])[NH:12][C:11]3[CH2:24][O:25][CH2:26][C:27](=[O:28])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8].BrN1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:10]3[C:27](=[O:28])[CH2:26][O:25][CH2:24][C:11]=3[NH:12][C:13]3[CH:20]([CH2:21][CH2:22][CH3:23])[O:17][C:15](=[O:16])[C:14]2=3)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18000980HCID 18000980, compound

Product 1

HCID 10202424HCID 10202424, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The product from Example 97B (0.77 g, 1.7 mmol) in chloroform (30 mL) under nitrogen was treated with N-bromosuccinimide (0.36 g, 2.0 mmol), stirred at ambient temperature for 30 minutes, refluxed for 16 hours and concentrated to dryness. The resulting two isomers were separated by chromatography on silica gel eluting with (ethyl acetate:formic acid:water:hexane, 38:1:1:40 to 38:1:1:30 to 38:1:1:20). The faster moving isomer was rechromatographed on silica gel eluting with 2% methanol in ammonia saturated dichloromethane and then rechromatographed again on silica gel eluting with (hexanes:acetone, 3:1). The faster moving isomer was then crystallized from acetone/hexanes and the resulting crystals were collected by filtration, washed with acetone/hexanes and dried under reduced pressure to provide the title compound (0.058 g).

Workup

  1. temperaturerefluxed for 16 hours
  2. concentrationconcentrated to dryness
  3. customThe resulting two isomers were separated by chromatography on silica gel eluting with (ethyl acetate:formic acid:water:hexane, 38:1:1:40 to 38:1:1:30 to 38:1:1:20)
  4. customwas rechromatographed on silica gel eluting with 2% methanol in ammonia saturated dichloromethane
  5. customrechromatographed again on silica gel eluting with (hexanes:acetone, 3:1)
  6. customwas then crystallized from acetone/hexanes
  7. filtrationthe resulting crystals were collected by filtration
  8. washwashed with acetone/hexanes
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-9d87aa2415634a7cad0ad30db6dbbb68
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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