Acetic Acid → (3R,5R)-tert-butyl 7-(2,5-diphenyl-4-(pyridin-4-yl)-1H-imidazol-1-yl)-3,5-dihydroxyheptanoate

HRID 1268703Notes

Reaction equation

HRID 1268703 reaction equation
O=[C:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:3]([NH:10][C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.C(O)(=O)C.[NH2:29][CH2:30][CH2:31][C@H:32]1[O:37]B(C2C=CC=CC=2)[O:35][C@@H:34]([CH2:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:33]1>C(O)C>[C:12]1([C:11]2[N:29]([CH2:30][CH2:31][C@@H:32]([OH:37])[CH2:33][C@@H:34]([OH:35])[CH2:44][C:45]([O:47][C:48]([CH3:49])([CH3:50])[CH3:51])=[O:46])[C:2]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:3]([C:4]3[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=3)[N:10]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11449985t-butyl 2-((4R,6R)-6-(2-aminoethyl)-2-phenyl-1,3,2-dioxaborinan-4-yl)acetateHCID 21075679N-(2-oxo-2-phenyl-1-(pyridin-4-yl)ethyl)benzamide2×

Product 1

HCID 58782243(3R,5R)-tert-butyl 7-(2,5-diphenyl-4-(pyridin-4-yl)-1H-imidazol-1-yl)-3,5-dihydroxyheptanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-(2-oxo-2-phenyl-1-(pyridin-4-yl)ethyl)benzamide, 67 (1.6 g) and acetic acid (1.5 mL) in ethanol (50 mL) is added tert-butyl 2-((4R,6R)-6-(2-aminoethyl)-2-phenyl-1,3,2-dioxaborinan-4-yl)acetate (7.9 g). Upon heating under reflux for 16 h, the solution is cooled to room temperature and the solvent is evaporated. The residue is partitioned between saturated aqueous sodium hydrogen carbonate and dichloromethane, the layers separated and the organic phase washed with brine, dried (magnesium sulfate), filtered and concentrated. Purification of the residue via chromatography affords the title compound, 68 (0.35 g).

Workup

  1. temperatureUpon heating
  2. temperatureunder reflux for 16 h
  3. customthe solvent is evaporated
  4. customThe residue is partitioned between saturated aqueous sodium hydrogen carbonate and dichloromethane
  5. customthe layers separated
  6. washthe organic phase washed with brine
  7. dry with materialdried (magnesium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification of the residue via chromatography

Sources & evidence

ORD record
ord-9a2f3cf842334fdeb5a898b7581690de
Source dataset
uspto-grants-2007_04
Patent number
US07199126B2

Reaction notes

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