Trifluoroacetic acid → 4-{[(6-(4-Fluorophenyl)-5-(methoxycarbonyl)-4-methyl-2-oxo-3,6-dihydro-1(2H)-pyrimidinyl)carbonyl]amino}butanoic acid

HRID 1452657Notes

Reaction equation

HRID 1452657 reaction equation
C([O:5][C:6](=[O:33])[CH2:7][CH2:8][CH2:9][NH:10][C:11]([N:13]1[CH:18]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:17]([C:26]([O:28][CH3:29])=[O:27])=[C:16]([CH3:30])[N:15]=[C:14]1[O:31]C)=[O:12])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:25][C:22]1[CH:23]=[CH:24][C:19]([CH:18]2[N:13]([C:11]([NH:10][CH2:9][CH2:8][CH2:7][C:6]([OH:33])=[O:5])=[O:12])[C:14](=[O:31])[NH:15][C:16]([CH3:30])=[C:17]2[C:26]([O:28][CH3:29])=[O:27])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57526926Methyl 1-{[(4-tert-butoxy-4-oxobutyl)amino]carbonyl}-6-(4-fluorophenyl)-2-methoxy-4-methyl-1,6-dihydro-5-pyrimidinecarboxylate

Product 1

HCID 575269344-{[(6-(4-Fluorophenyl)-5-(methoxycarbonyl)-4-methyl-2-oxo-3,6-dihydro-1(2H)-pyrimidinyl)carbonyl]amino}butanoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of methyl 1-{[(4-tert-butoxy-4-oxobutyl)amino]carbonyl}-6-(4-fluorophenyl)-2-methoxy-4-methyl-1,6-dihydro-5-pyrimidinecarboxylate (77.3 mg, 0.166 mmol) in dichloromethane (2.00 mL) at 0° C. was slowly added trifluoroacetic acid (189 mg, 1.66 mmol). The reaction mixture was stirred at room temperature for 10 min and concentrated in vacuo. The residue was dissolved in iso-PrOH/CHCl3 (1:3, 10 mL) and basified to pH 11 with 10% KOH solution, washed with H2O, followed by brine. The organic layer was dried over MgSO4 and concentrated in vacuo to afford the desired product (58.1 mg, 88.9%). ESMS m/e: 394.1 (M+H)+.

Workup

  1. customat 0° C.
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in iso-PrOH/CHCl3 (1:3, 10 mL)
  4. washwashed with H2O
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05b354e7b8e0445fa34db530845ea4af
Source dataset
uspto-grants-2009_01
Patent number
US07473698B2

Reaction notes

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