Sodium Hydroxide → 2-(2-Fluoro-phenoxy)-2-methyl-3-(4-{2-[3-methyl-2-oxo-1-(3-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid

HRID 1985136Notes

Reaction equation

HRID 1985136 reaction equation
C([O:3][C:4](=[O:43])[C:5]([O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[F:42])([CH3:34])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)[C:18](=[O:32])[N:17]2[CH3:33])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[F:42][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[O:35][C:5]([CH3:34])([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:30])([F:31])[F:29])[CH:23]=3)[C:18](=[O:32])[N:17]2[CH3:33])=[CH:11][CH:12]=1)[C:4]([OH:43])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68867419HCID 68867419, compound

Product 1

HCID 101966892-(2-Fluoro-phenoxy)-2-methyl-3-(4-{2-[3-methyl-2-oxo-1-(3-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(2-Fluoro-phenoxy)-2-methyl-3-(4-{2-[3-methyl-2-oxo-1-(3-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid ethyl ester and 5N NaOH (0.2 mL) in ethanol (2 mL) is refluxed under nitrogen for 1 h, cooled to ambient temperature, and concentrated in vacuo. The residue is diluted with 1N HCl, extracted with CH2Cl2, dried, concentrated in vacuo, and purified by LCMS to provide the title compound. 1H NMR (400 MHz, CDCl3): δ 7.53-7.42 (m, 2H), 7.29-6.93 (m, 7H), 6.85-6.73 (m, 3H), 4.49-4.29 (m, 2H), 3.99-3.95 (m, 2H), 3.81-3.68 (m, 1H), 3.46-3.41 (m, 1H), 3.28, 3.16 (ABq, 2H, J=13.7 Hz), 3.09-3.04 (m, 1H), 2.86 (d, 3H, J=5.6 Hz), 2.25-2.21 (m, 1H), 1.93-1.87 (m, 1H), 1.40 (s, 3H). MS [ES+] m/z exact mass calcd for C30H31N2O5F4 575.2169, found 575.2156.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue is diluted with 1N HCl
  3. extractionextracted with CH2Cl2
  4. customdried
  5. concentrationconcentrated in vacuo
  6. custompurified by LCMS

Sources & evidence

ORD record
ord-8d38a2689e694a998b50efda288f2782
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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