Sodium Hydroxide → HCID 178493442, compound

HRID 1526514Notes

Reaction equation

HRID 1526514 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[NH:12][C:13]([C:16]([OH:28])([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:17](OC)=[O:18])=[N:14][N:15]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[OH-].[Na+].[F:31][C:32]1[CH:37]=[CH:36][C:35]([C@H:38]([N:40]=[C:41]=[O:42])[CH3:39])=[CH:34][CH:33]=1>C1COCC1.C(OCC)(=O)C>[CH2:21]([C:16]1([C:13]2[NH:12][C:11]([C:5]3[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)=[N:15][N:14]=2)[O:28][C:41](=[O:42])[N:40]([C@@H:38]([C:35]2[CH:34]=[CH:33][C:32]([F:31])=[CH:37][CH:36]=2)[CH3:39])[C:17]1=[O:18])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 7018263(R)-(+)-1-(4-Fluorophenyl)ethyl isocyanateHCID 178501796HCID 178501796, compound

Product 1

HCID 178493442HCID 178493442, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-[5-(3,5-dimethoxyphenyl)-4H-1,2,4-triazol-3-yl]-2-hydroxy-3-phenylpropanoate (7 mg) in 1 mL of THF was added NaOH (4 mg) and (R)-1-fluoro-4-(1-isocyanatoethyl)benzene (15 mg). The resulting mixture was stirred at ambient temperature overnight. The resulting mixture was diluted with ethyl acetate, and then quenched with water. The organic layer was concentrated and purified by reverse phase HPLC (YMC Pro-C18 column, gradient elution, 30% to 100% acetonitrile/water with 0.1% TFA) to give the title compound. LC/MS 517.2 (M+1). IC50 value=C rating.

Workup

  1. customquenched with water
  2. concentrationThe organic layer was concentrated
  3. custompurified by reverse phase HPLC (YMC Pro-C18 column, gradient elution, 30% to 100% acetonitrile/water with 0.1% TFA)

Sources & evidence

ORD record
ord-372c1d60390f42c0b6abc50d098d57e9
Source dataset
uspto-grants-2015_07
Patent number
US09085568B2

Reaction notes

Loading…