Sodium Hydroxide → HCID 68869631, compound

HRID 1985161Notes

Reaction equation

HRID 1985161 reaction equation
C([O:3][C:4](=[O:39])[C:5]([O:36][CH2:37][CH3:38])([CH3:35])[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]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)[C:18](=[O:33])[N:17]2[CH3:34])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[CH2:37]([O:36][C:5]([CH3:35])([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]([O:28][C:29]([F:31])([F:32])[F:30])=[CH:26][CH:27]=3)[C:18](=[O:33])[N:17]2[CH3:34])=[CH:11][CH:12]=1)[C:4]([OH:39])=[O:3])[CH3:38]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68867604HCID 68867604, compound

Product 1

HCID 68869631HCID 68869631, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-ethoxy-2-methyl-3-(4-{2-[3-methyl-2-oxo-1-(4-trifluoromethoxy-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid ethyl ester and 5N NaOH (0.3 mL) in ethanol (3 mL) is refluxed for 1 h, cooled to ambient temperature, and concentrated. The residue is diluted with CH2Cl2, dried, and concentrated in vacuo to provide the title compound (0.022 g, 32% after two steps). 1H NMR (400 MHz, CDCl3): δ 7.24-7.19 (m, 1H), 7.09 (d, 2H, J=8.3 Hz), 6.83-6.78 (m, 3H), 6.69 (d, 2H, J=8.3 Hz), 4.38, 4.28 (ABq, 2H, J=14.8 Hz), 3.94-3.91 (m, 3H), 3.77 (s, 3H), 3.60-3.53 (m, 3H), 3.36 (t, 1H, J=9.0 Hz), 3.04-2.92 (m, 1H), 1.89-1.83 (m, 1H), 1.40 (s, 3H), 1.23 (t, 3H, J=6.9 Hz). MS [EI+] 525 (M+H)+, [EI−] 523 (M−H)+. Rf=0.27 in 10% CH3OH in CH2Cl2.

Workup

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

Sources & evidence

ORD record
ord-529a4b4a703442818274837026dffa26
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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