Hydrogen Bromide → HCID 44624284, compound

HRID 2390831Notes

Reaction equation

HRID 2390831 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:18]2[C:19]([O:24]C)=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:8]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Br.C([O-])(O)=O.[Na+]>CC(O)=O>[C:1]([C:5]1[CH:6]=[C:7]([C:18]2[C:19](=[O:24])[NH:20][CH:21]=[CH:22][CH:23]=2)[CH:8]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 67069984HCID 67069984, compound

Product 1

HCID 44624284HCID 44624284, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

step 2—A solution of 124 (52 mg, 0.157 mmol), 48% HBr (50 □L, 0.436 mmol) and HOAc (3 mL) in sealed tube was heated at 70° C. overnight. The reaction mixture was cooled to RT, carefully poured into a cold saturated aqueous NaHCO3 and then extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified on a preparative SiO2 TLC plate developed with 66% EtOAc/hexanes to afford 48 mg (96%) of I-45 as a foam.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified on a preparative SiO2 TLC plate
  7. customto afford 48 mg (96%) of I-45 as a foam

Sources & evidence

ORD record
ord-bd634f144abb417690344ecbc4a2e33b
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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