Potassium Carbonate → t-Butyloxycarbonyl(4'-chlorobiphenyl-4-sulfonylamino]-4-(3,4,4-trimethyl-2,5-dioxoimidazolin-1-yl)butyric acid t-butyl ester

HRID 651331Notes

Reaction equation

HRID 651331 reaction equation
[C:1]([O:5][C:6](=[O:35])[C@H:7]([N:11](C(OC(C)(C)C)=O)[S:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH2:8][CH2:9]I)([CH3:4])([CH3:3])[CH3:2].[CH3:36][N:37]1[C:41]([CH3:43])([CH3:42])[C:40](=[O:44])[NH:39][C:38]1=[O:45].[C:46](=[O:49])([O-])[O-:47].[K+].[K+]>CN(C=O)C.C1OCCOCCOCCOCCOCCOC1>[C:1]([O:47][C:46](=[O:49])[C:7]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:35])([NH:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:19][CH:20]=1)(=[O:13])=[O:14])[CH2:8][CH2:9][N:39]1[C:40](=[O:44])[C:41]([CH3:43])([CH3:42])[N:37]([CH3:36])[C:38]1=[O:45])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 812951,5,5-Trimethylimidazolidine-2,4-dioneHCID 53729423(2R)-[t-butyloxycarbonyl(4'-chlorobiphenyl-4-sulfonyl)amino]-4-iodobutyric acid t-butyl ester

Product 1

HCID 131722835t-Butyloxycarbonyl(4'-chlorobiphenyl-4-sulfonylamino]-4-(3,4,4-trimethyl-2,5-dioxoimidazolin-1-yl)butyric acid t-butyl esterYield 41%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of the title F compound, (2R)-[t-butyloxycarbonyl(4′-chlorobiphenyl-4-sulfonyl)amino]-4-iodobutyric acid t-butyl ester (0.6 g, 0.94 mmol) in 10 mL DMF is added 3,4,4-trimethyl-2,5-dioxoimidazoline and potassium carbonate (0.65 g, 4.72 mmol) followed by 2 mg of 18-crown-6. The reaction mixture is stirred at room RT for 3 h, then partitioned between water and EtOAc. The organic solution is washed with brine, dried over anhydrous Na2SO4 and concentrated. Chomatography on silica gel (eluant; 1/19—EtOAc/hexane) affords the title compound as a white foam (0.25 g, 41%).

Workup

  1. custompartitioned between water and EtOAc
  2. washThe organic solution is washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-00cf6f5262e34da39906dac16dcbf992
Source dataset
uspto-grants-2001_08
Patent number
US06277987B1

Reaction notes

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