Sodium Hydroxide → HCID 58978946, compound

HRID 1181075Notes

Reaction equation

HRID 1181075 reaction equation
[C:1]([O:5][C:6](=[O:39])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30][N:31](C)[C:32](=O)C(F)(F)F)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.C1COCC1>[C:1]([O:5][C:6](=[O:39])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30][NH:31][CH3:32])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 589793073-(4-[2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethoxy]-2-{[methyl-(2,2,2-trifluoro-acetyl)-amino]-methyl}-phenyl)-propionic acid tert-butyl ester

Product 1

HCID 58978946HCID 58978946, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 3-(4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-2-{[methyl-(2,2,2-trifluoro-acetyl)-amino]-methyl}-phenyl)-propionic acid tert-butyl ester (111 mg, 0.20 mmol) in methanol (5 mL) and THF (5 mL) was treated with 2N NaOH (1.0 mL, 2.0 mmol) and heated at 55° C. for 1 h. The reaction mixture was cooled, concentrated, neutralized with 1N HCl and extracted into EtOAc. The organic layer was washed with saturated NaHCO3 solution and brine, dried (Na2SO4), and concentrated. The residue was purified by silica gel radial chromatography (CH2Cl2/methanol 95/5 to 90/10) to the title compound (37 mg, 42%). MS (ES) m/z 451.3 [M+1].

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. extractionextracted into EtOAc
  4. washThe organic layer was washed with saturated NaHCO3 solution and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel radial chromatography (CH2Cl2/methanol 95/5 to 90/10) to the title compound (37 mg, 42%)

Sources & evidence

ORD record
ord-462e3706aef14b65961e68aabd13575a
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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