2-(4-{3-[1-(3,4-Dimethyl-benzyl)-2,5-dioxo-imidazolidin-4-yl]-propyl}-phenoxy)-2-methyl-propionic acid tert-butyl ester → 2-(4-{3-[1-(3,4-Dimethyl-benzyl)-2-oxo-imidazolidin-4-yl]-propyl}-phenoxy)-2-methyl-propionic acid tert-butyl ester

HRID 1985246

Reaction equation

HRID 1985246 reaction equation
[C:1]([O:5][C:6](=[O:36])[C:7]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH:20]2[C:24](=O)[N:23]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([CH3:34])[CH:28]=3)[C:22](=[O:35])[NH:21]2)=[CH:13][CH:12]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([O:5][C:6](=[O:36])[C:7]([O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][CH2:19][CH:20]2[CH2:24][N:23]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([CH3:34])[CH:28]=3)[C:22](=[O:35])[NH:21]2)=[CH:15][CH:16]=1)([CH3:8])[CH3:9])([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 1

HCID 577190872-(4-{3-[1-(3,4-Dimethyl-benzyl)-2,5-dioxo-imidazolidin-4-yl]-propyl}-phenoxy)-2-methyl-propionic acid tert-butyl ester

Product 1

HCID 577188972-(4-{3-[1-(3,4-Dimethyl-benzyl)-2-oxo-imidazolidin-4-yl]-propyl}-phenoxy)-2-methyl-propionic acid tert-butyl esterYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(4-{3-[1-(3,4-dimethyl-benzyl)-2,5-dioxo-imidazolidin-4-yl]-propyl}-phenoxy)-2-methyl-propionic acid tert-butyl ester (0.113 g, 0.228 mmol) in THF (6 mL) was treated dropwise with 1 M solution of borane-THF complex in THF (4.4 mL, 4.4 mmol) and then stirred at room temperature under N2 for 32 h. The reaction was quenched with methanol (6 mL) and stirred at room temperature for 2 hr. The solvent was removed in vacuo to give crude product that was purified by flash chromatography using 97:3 CH2Cl2:MeOH to afford 0.051 g (47%) 2-(4-{3-[1-(3,4-dimethyl-benzyl)-2-oxo-imidazolidin-4-yl]-propyl}-phenoxy)-2-methyl-propionic acid tert-butyl ester. MS (ES+) Calc'd for C29H41N2O4 (M+1) 481. Found m/z 481 (100%). 1H NMR.

Workup

  1. customThe reaction was quenched with methanol (6 mL)
  2. stirringstirred at room temperature for 2 hr
  3. customThe solvent was removed in vacuo
  4. customto give crude product that
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-69cd10ab803340919d385eae1884b3fe
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Linked notes

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