Lithium Hydroxide → HCID 178463865, compound

HRID 333418Notes

Reaction equation

[CH2:1]([N:3]([CH2:21][CH2:22][C:23]1[N:24]=[CH:25][NH:26][CH:27]=1)[C:4](=[O:20])[NH:5][C@@H:6]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:7]([O:9]C)=[O:8])[CH3:2].[OH-].[Li+]>C1COCC1.O>[CH2:1]([N:3]([CH2:21][CH2:22][C:23]1[N:24]=[CH:25][NH:26][CH:27]=1)[C:4](=[O:20])[NH:5][CH:6]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[C:7]([OH:9])=[O:8])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

150 mg (0.4 mmol) of methyl(S)-2-{3-ethyl-3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propionate are diluted in 4 mL of THF and 1 mL of water, and 150 mg (6 mmol) of lithium hydroxide are added. The mixture is heated for 10 minutes at 100° C. in a microwave reactor. The solvents are evaporated off and the residue is then purified on a pad of silica (eluent: 1/1 dichloromethane/methanol). 100 mg of 2-{3-ethyl-3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propionic acid in the form of a pale yellow powder are obtained in a yield of 69%.

Workup

customThe solvents are evaporated off
customthe residue is then purified on a pad of silica (eluent: 1/1 dichloromethane/methanol)

Sources & evidence

ORD record: ord-693d2af3870b46c687b562cc960d4560
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877968B2

Reaction notes

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