Phosphate → HCID 59377724, compound

HRID 1691818Notes

Reaction equation

HRID 1691818 reaction equation
C([O:5][C:6](=[O:33])[C:7]1[CH:12]=[C:11]([Br:13])[C:10]([NH:14][C:15]([N:17]2[CH:22]=[CH:21][C:20](=[O:23])[CH2:19][C@H:18]2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[O:16])=[CH:9][C:8]=1[O:31][CH3:32])(C)(C)C.FC(F)(F)C(O)=O.P([O-])([O-])([O-])=O>ClCCl>[Br:13][C:11]1[C:10]([NH:14][C:15]([N:17]2[CH:22]=[CH:21][C:20](=[O:23])[CH2:19][C@H:18]2[C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)=[O:16])=[CH:9][C:8]([O:31][CH3:32])=[C:7]([CH:12]=1)[C:6]([OH:33])=[O:5]

Participants

5

Reactant 3

HCID 1061PhosphateHCID 6422Trifluoroacetic acidHCID 59377798HCID 59377798, compound

Product 1

HCID 59377724HCID 59377724, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-5-Bromo-4-{[2-(4-fluoro-phenyl)-4-oxo-3,4-dihydro-2H-pyridine-1-carbonyl]-amino}-2-methoxy-benzoic acid tert-butyl ester (170 mg) was stirred in 10 ml dichloromethane with 0.1 ml trifluoroacetic acid for 5 hours. Phosphate buffer (pH 7) was added, the layers separated, and the dichloromethane removed in vacuo. The residue was dissolved in acetone and recrystallized by slow addition of water. The crystals were filtered and dried to give 108 mg of (S)-5-bromo-4-{[2-(4-fluoro-phenyl)-4-oxo-3,4-dihydro-2H-pyridine-1-carbonyl]-amino}-2-methoxy-benzoic acid.

Workup

  1. customthe layers separated
  2. customthe dichloromethane removed in vacuo
  3. dissolutionThe residue was dissolved in acetone
  4. customrecrystallized by slow addition of water
  5. filtrationThe crystals were filtered
  6. customdried

Sources & evidence

ORD record
ord-7c1dfa499e22428dac11560f311fdd11
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

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