Water → HCID 25175312, compound

HRID 2190338Notes

Reaction equation

HRID 2190338 reaction equation
[CH:1]1([CH2:7][CH2:8][NH:9][CH2:10][CH2:11][CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:25][O:26][C:27](=[O:37])[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([N:34]=[C:35]=[O:36])[CH:29]=1.O>C(Cl)Cl>[CH3:25][O:26][C:27](=[O:37])[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH:34][C:35]([N:9]([CH2:8][CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:10][CH2:11][CH:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:36])[CH:29]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2733366Methyl 3-isocyanatobenzoateHCID 57586408HCID 57586408, compound

Product 1

HCID 25175312HCID 25175312, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

46 mg of (2-cyclohexyl-ethyl)-(3,3-diphenyl-propyl)-amine (0.147 mmol, 1 eq) were diluted in 1 mL of DCM. 30 mg (0.172 mmol, 1.2 eq) of 3-isocyanato-benzoic acid methyl ester were then added to the mixture. The reaction mixture was stirred at room temperature for 90 min before adding water, then the aqueous phase was extracted with DCM. The organic phase was washed with water, brine, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography over silica gel (eluant: gradient Hept/EtOAc 5/1). 63 mg of the desired urea were obtained. MS (ES+): 499.5+ (M+H)+. TLC: Rf: 0.57 (eluant: heptane/EtOAc: 1/1).

Workup

  1. extractionthe aqueous phase was extracted with DCM
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography over silica gel (eluant: gradient Hept/EtOAc 5/1)

Sources & evidence

ORD record
ord-e41db223360e411ea447cae20585d180
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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