Sodium Hydroxide → HCID 10196028, compound

HRID 1985160Notes

Reaction equation

HRID 1985160 reaction equation
C([O:3][C:4](=[O:38])[C:5]([O:35][CH2:36][CH3:37])([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][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)[C:18](=[O:32])[N:17]2[CH3:33])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[CH2:36]([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:23]=[CH:24][C:25]([C:28]([F:30])([F:29])[F:31])=[CH:26][CH:27]=3)[C:18](=[O:32])[N:17]2[CH3:33])=[CH:11][CH:12]=1)[C:4]([OH:38])=[O:3])[CH3:37]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68869663HCID 68869663, compound

Product 1

HCID 10196028HCID 10196028, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-Ethoxy-2-methyl-3-(4-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid ethyl ester (0.19 g, 0.347 mmol) and 5N NaOH (0.5 mL) in ethanol (5 mL) is refluxed for 1 h, cooled to ambient temperature, and concentrated. The residue is diluted with CH2Cl2, washed, dried, and concentrated in vacuo to provide the title compound. 1H NMR (400 MHz, CDCl3): δ 7.63 (d, 2H, J=8.4 Hz), 7.44 (d, 2H, J=8.4 Hz), 7.08 (d, 2H, J=8.7 Hz), 6.76 (d, 2H, J=8.7 Hz), 4.37, 4.35 (ABq, 2H, J=16.4 Hz), 3.99-3.89 (m, 2H), 3.63-3.53 (m, 1H), 3.43-3.23 (m, 2H), 2.98 (t, 1H, J=8.8 Hz), 2.86, 2.84 (ABq, 2H, J=15.4 Hz), 2.71 (s, 3H), 2.51-2.49 (m, 3H), 2.23-2.13 (m, 1H), 1.86-1.74 (m, 1H), 1.15 (s, 3H), 1.08 (t, 3H, J=6.9 Hz). MS [ES+] m/z exact mass calcd for C26H32N2O5F3 509.2263, found 509.2288.

Workup

  1. concentrationconcentrated
  2. additionThe residue is diluted with CH2Cl2
  3. washwashed
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f0ebde1fced4ddd9b3bbece79b5c469
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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