Water → methyl(S)-2-[3-(1H-imidazol-4-ylmethyl)ureido]-3-(4-methoxy-phenyl)propanoate

HRID 333443Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@H:10]([NH:15][C:16]([O:18]C2C=CC([N+]([O-])=O)=CC=2)=O)[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.Cl.Cl.[NH:39]1[CH:43]=[C:42]([CH2:44][NH2:45])[N:41]=[CH:40]1.O>CN(C)C=O>[NH:39]1[CH:43]=[C:42]([CH2:44][NH:45][C:16](=[O:18])[NH:15][C@@H:10]([CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:11]([O:13][CH3:14])=[O:12])[N:41]=[CH:40]1

Participants

Conditions

Temperature: 80 °C

Procedure

1.1 g (0.37 mmol) of methyl(S)-3-(4-methoxyphenyl)-2-(4-nitrophenoxycarbonyl-amino)propanoate (cf. preparation 2-2) and 0.7 mL (0.37 mmol) of diisopropyl-ethylamine in 5 mL of dimethylformamide are added at 80° C. to a solution of 500 mg (0.37 mmol) of C-(1H-imidazol-4-yl)methylamine dihydrochloride in 15 mL of dimethylformamide. The reaction mixture is stirred for 2 hours at 80° C. The reaction is stopped by adding 30 mL of water and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (eluent: 80/20 dichloromethane/methanol). 279 mg of methyl (S)-2-[3-(1H-imidazol-4-yl-methyl)-ureido]-3-(4-methoxyphenyl)propanoate in the form of a yellow oil are obtained in a yield of 63%.

Workup

extractionextracted with ethyl acetate
dry with materialdried over sodium sulfate
customThe solvents are evaporated off
customthe residue is then chromatographed on silica gel (eluent: 80/20 dichloromethane/methanol)

Sources & evidence

ORD record: ord-77901112944140f4815ffd680bf041ff
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877968B2

Reaction notes

Loading…