Potassium Iodide → 3-[3-(1-tert-butoxycarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)ureido]benzoic acid

HRID 1979483Notes

Reaction equation

HRID 1979483 reaction equation
C(OC(=O)CBr)(C)(C)C.[C:10]([O:14][C:15]([CH2:17][N:18]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]([CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:21][CH:20]([NH:35][C:36]([NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([O:47]CC3C=CC=CC=3)=[O:46])[CH:40]=2)=[O:37])[C:19]1=[O:55])=[O:16])([CH3:13])([CH3:12])[CH3:11].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].O=C1NC2C=CC=CC=2N(C2CCCCC2)CC1NC(NC1C=CC=C(C(OCC2C=CC=CC=2)=O)C=1)=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O>[C:10]([O:14][C:15]([CH2:17][N:18]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]([CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:21][CH:20]([NH:35][C:36](=[O:37])[NH:38][C:39]2[CH:40]=[C:41]([CH:42]=[CH:43][CH:44]=2)[C:45]([OH:47])=[O:46])[C:19]1=[O:55])=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 212017761-(1-tert-butoxycarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea Tert-butyl bromoacetateHCID 212018741-(2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea

Product 1

HCID 212019863-[3-(1-tert-butoxycarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)ureido]benzoic acidYield 295.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Preparation of 1-(1-tert-butoxycarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea Tert-butyl bromoacetate (503 mg), potassium iodide (23 ml), tetra n-butylammonium bromide (23 mg) and potassium carbonate (713 mg) were added to a solution of 1-(2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea (800 mg) in dimethylsulfoxide (10 ml), the mixture was stirred at room temperature for one hour. Ice-water was added thereto, extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:2), to thereby obtain 970 mg of the titled compound (Yield: 90%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:2)

Sources & evidence

ORD record
ord-781f2416c743401180355aaede82e3e7
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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