Toluene → HCID 178463866, compound

HRID 333417Notes

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.Cl.[CH2:29]([NH:31][CH2:32][CH2:33][C:34]1[N:35]=[CH:36][NH:37][CH:38]=1)[CH3:30].C(N(C(C)C)CC)(C)C.C1(C)C=CC=CC=1>CN(C=O)C>[CH2:29]([N:31]([CH2:32][CH2:33][C:34]1[N:35]=[CH:36][NH:37][CH:38]=1)[C:16](=[O:18])[NH:15][C@@H:10]([CH2:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:11]([O:13][CH3:14])=[O:12])[CH3:30]

Participants

Conditions

Temperature: 80 °C

Procedure

0.14 g (0.38 mmol) of methyl(S)-3-(4-methoxyphenyl)-2-(4-nitrophenoxycarbonyl-amino)propionate is diluted in 2 mL of DMF. The solution is heated to 80° C. and 0.16 g (0.76 mmol) of ethyl[2-(1H-imidazol-4-yl)ethyl]amine hydrochloride and 0.13 mL (1.3 mmol) of diisopropylethylamine are then added. After 5 minutes, the reaction medium is cooled to room temperature and stirred for 15 minutes. Toluene is added and the solvents are evaporated off. The crude product obtained is chromatographed on silica gel (eluent: 8/2 dichloromethane/methanol). 0.15 g of methyl(S)-2-{3-ethyl-3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)-propionate in the form of a colourless oil is obtained in a yield of 100%.

Workup

temperaturethe reaction medium is cooled to room temperature
customthe solvents are evaporated off
customThe crude product obtained
customis chromatographed on silica gel (eluent: 8/2 dichloromethane/methanol)

Sources & evidence

ORD record: ord-03d5dba057ec4eac8acbebaeced614f0
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877968B2

Reaction notes

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