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

HRID 1985258Notes

Reaction equation

HRID 1985258 reaction equation
C1([O:6][C:7](=[O:43])[CH:8]([O:37][CH:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH:19]3[CH2:23][N:22]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)[C:21](=[O:35])[N:20]3[CH3:36])=[CH:12][CH:11]=2)CCCC1.[OH-].[Na+]>C(O)C>[CH:38]1([O:37][CH:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH:19]3[CH2:23][N:22]([CH2:24][C:25]4[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:29][CH:30]=4)[C:21](=[O:35])[N:20]3[CH3:36])=[CH:12][CH:11]=2)[C:7]([OH:43])=[O:6])[CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 688693802-Cyclopentyloxy-3-(4-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid cyclopentyl ester

Product 1

HCID 688688522-Cyclopentyloxy-3-(4-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-cyclopentyloxy-3-(4-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid cyclopentyl ester (0.108 g, 0.179 mmol) in ethanol (10 mL) was treated with aqueous 5 N NaOH (1 mL) and stirred at room temperature for 3 h. The solvent removed in vacuo. The resultant residue was acidified with aqueous 1 N HCl (10 mL) and extracted with CH2Cl2. The organic layer was dried (Na2SO4) and the solvent removed in vacuo to afford 0.106 g of crude acid that was purified by chiral HPLC (20×250 nm Chiralpak AD, 3:2 heptane:IPA with 0.1% trifluoroacetic acid mobile phase, 14 mL/min, 225 nm) to give 0.080 g (83%) of 100% de 2-cyclopentyloxy-3-(4-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid. 1H NMR. HRMS (ES+) m/z exact mass calc'd for C28H34N2O5F3 (M+1) 535.2420. Found m/z 535.2408.

Workup

  1. customThe solvent removed in vacuo
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe solvent removed in vacuo
  5. customto afford 0.106 g of crude acid that
  6. customwas purified by chiral HPLC (20×250 nm Chiralpak AD, 3:2 heptane:IPA with 0.1% trifluoroacetic acid mobile phase, 14 mL/min, 225 nm)

Sources & evidence

ORD record
ord-89c7e4295926466d9c924e4e6c3fc82b
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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