3-Phenylpropyl isocyanate → Ethyl 3-{3'-[1-methyl-3-(3-phenylpropyl)ureido]biphenyl-4-yl}propanoate

HRID 250862Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

188 μL (1.2 mmol, 1.5 eq) 3-phenylpropyl isocyanate are added to a solution of 230 mg (0.81 mmol, 1 eq) of ethyl 3-(3′-methylaminobiphenyl-4-yl)propanoate (prepared in Example 7c) in 10 mL of an 8/2 dichloromethane/triethylamine mixture. The reaction medium is stirred at 40° C. for 12 hours and then hydrolyzed with water and extracted with ethyl acetate. The organic phases are combined, washed with sodium chloride solution and dried over sodium sulfate. The solvents are evaporated off and the residual oil is chromatographed on silica (7/3 heptane/ethyl acetate). 348 mg of ethyl 3-{3′-[1-methyl-3-(3-phenylpropyl)ureido]biphenyl-4-yl}propanoate are obtained in solid form. Yield=96%

Workup

extractionhydrolyzed with water and extracted with ethyl acetate
washwashed with sodium chloride solution
dry with materialdried over sodium sulfate
customThe solvents are evaporated off
customthe residual oil is chromatographed on silica (7/3 heptane/ethyl acetate)

Sources & evidence

ORD record: ord-a1543b0243a846b2837b49971130c72e
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863332B2

Reaction notes

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