Acetic Acid → HCID 178524215, compound

HRID 383782Notes

Reaction equation

HRID 383782 reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([C:15]([O:17]C)=[O:16])[CH:12]=[CH:11][C:10]=2[C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=2)=[CH:5][CH:4]=1.C(O)(=O)C.C([O-])(O)=O.[Na+]>Br>[OH:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[CH:11][C:10]=2[C:19]2[CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=[C:21]([C:29]([F:32])([F:30])[F:31])[CH:20]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 86657758HCID 86657758, compound

Product 1

HCID 178524215HCID 178524215, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 11a (240 mg, 0.527 mmol) in hydrobromic acid (5.00 mL of a 33 wt. % acetic acid solution) was heated to 60° C. in a sealed tube. After 20 h, the reaction mixture was cooled to rt and was added to said. aq. NaHCO3. The resulting mixture was extracted with EtOAc, and combined organics were concentrated in vacuo to give a crude residue that was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier), followed by lyophilization of the purified fractions to afford the title compound 11b. m/z (ES) 428 (MH)+.

Workup

  1. additionwas added
  2. extractionThe resulting mixture was extracted with EtOAc
  3. concentrationcombined organics were concentrated in vacuo
  4. customto give a crude residue that
  5. customwas purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier)

Sources & evidence

ORD record
ord-761424738be449b58716bffff20c202c
Source dataset
uspto-grants-2013_02
Patent number
US08367679B2

Reaction notes

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