3-(2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid tert-butyl ester → 3-(2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid

HRID 1985210Notes

Reaction equation

HRID 1985210 reaction equation
C([O:5][C:6](=[O:48])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH:18]2[CH2:22][N:21]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)[C:20](=[O:34])[N:19]2[CH3:35])=[CH:11][C:10]=1[CH2:36][N:37]1[C:45](=[O:46])[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:38]1=[O:47])(C)(C)C>C(Cl)Cl>[O:47]=[C:38]1[C:39]2[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:45](=[O:46])[N:37]1[CH2:36][C:10]1[CH:11]=[C:12]([O:15][CH2:16][CH2:17][CH:18]2[CH2:22][N:21]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)[C:20](=[O:34])[N:19]2[CH3:35])[CH:13]=[CH:14][C:9]=1[CH2:8][CH2:7][C:6]([OH:48])=[O:5]

Participants

3

Reactant 1

HCID 688675093-(2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid tert-butyl ester

Product 1

HCID 102187663-(2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acidYield 50.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the ester obtained in Step A (70 mg, 0.10 mmol) in trifluoroacetic (1 ml) and methylene chloride (2 ml) is stirred at 23° C. for 7 hours. Concentration of the reaction mixture gave an oil which is partitioned between ethyl acetate (20 ml) and water (25 ml). The ethyl acetate layer is washed with water (15 ml), brine (20 ml), dried (Na2SO4), and concentrated to an oil which is purified by chromatography on a Biotage silica cartridge (gradient elution, 100% methylene chloride to 10:1 methylene chloride:methanol) to produce an oil (31 mg, 48%).

Workup

  1. customConcentration of the reaction mixture gave an oil which
  2. customis partitioned between ethyl acetate (20 ml) and water (25 ml)
  3. washThe ethyl acetate layer is washed with water (15 ml), brine (20 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to an oil which
  6. customis purified by chromatography on a Biotage silica cartridge (gradient elution, 100% methylene chloride to 10:1 methylene chloride:methanol)

Sources & evidence

ORD record
ord-0bae457e6b974f3c8873647b4a1c15f9
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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