Potassium Cyanide → 5-(1-(Benzyloxycarbonylamino)-2-(3-tert-butyl-4-hydroxylphenyl)ethyl)imidazolidine-2,4-dione

HRID 1988263Notes

Reaction equation

[NH:1]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C@H:2](C=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.[C-:27]#[N:28].[K+].[C:30](=[O:33])([O-])[O-].[NH4+:34].[NH4+].[C:36]([O-:39])(O)=O.[Na+]>C(O)C.O>[CH2:20]([O:19][C:17]([NH:1][CH:2]([CH:27]1[NH:28][C:36](=[O:39])[NH:34][C:30]1=[O:33])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:13])([CH3:14])[CH3:12])[CH:5]=1)=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of Z-Tyr(3-tBu)-H (2.18 g, 6.14 mmol) in ethanol (25 ml), potassium cyanide (480 mg, 7.37 mmol), 30% ammonium carbonate (1.77 g, 18.4 mmol) and water (25 ml) were added and stirred at 60° C. for 8 hours. The mixture was left for cooling and mixed with a saturated aqueous NaHCO3 solution. The organic layer was extracted with ethyl acetate and washed with water and then with saturated brine, dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:1), giving the titled compound (1.38 g, 53%).

Workup

waitThe mixture was left
temperaturefor cooling
extractionThe organic layer was extracted with ethyl acetate
washwashed with water
dry with materialwith saturated brine, dried over anhydrous magnesium sulfate
customevaporated
customto remove the solvent under reduced pressure

Sources & evidence

ORD record: ord-40279afe26a94e37b0d9304f545ce29d
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07553969B1

Reaction notes

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