Potassium Hydroxide → HCID 17795698, compound

HRID 1859854Notes

Reaction equation

[OH-].[K+].[O:3]([CH2:10][CH2:11][CH:12]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][NH:28][C:29](=[O:42])[C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)=[CH:32][CH:31]=2)=[CH:21][CH:20]=1)[C:13]([O:15]CC)=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[O:3]([CH2:10][CH2:11][CH:12]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][NH:28][C:29](=[O:42])[C:30]2[CH:31]=[CH:32][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)=[CH:34][CH:35]=2)=[CH:21][CH:20]=1)[C:13]([OH:15])=[O:14])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

An aqueous solution of potassium hydroxide (85%, 0.13 g) was added to a solution of ethyl 2-(2-phenoxyethyl)-3-[4-[2-(4-pyridine-2-ylbenzoylamino)ethoxy]phenyl]propionate (350 mg) in ethanol (8 ml). The mixture was stirred at 80° C. for 3 hours. At the end of this time the ethanol was evaporated under reduced pressure. An aqueous solution of hydrogen chloride (1N, 2.0 ml) and ethyl acetate was added to the residue. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (260 mg) as a mass of foam.

Workup

customAt the end of this time the ethanol was evaporated under reduced pressure
additionAn aqueous solution of hydrogen chloride (1N, 2.0 ml) and ethyl acetate was added to the residue
customThe ethyl acetate layer was separated
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-62963417885740f0a5c1653bac244730
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528525B1

Reaction notes

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