Potassium Hydroxide → HCID 18626620, compound

HRID 1860162Notes

Reaction equation

C([O:3][C:4](=[O:28])[CH2:5][CH2:6][NH:7][C:8]([NH:10][C:11](=[O:27])[CH:12]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)[CH2:13][CH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:9])C.[OH-].[K+]>C(O)C.O>[CH:14]1([CH2:13][CH:12]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[C:11]([NH:10][C:8](=[O:9])[NH:7][CH2:6][CH2:5][C:4]([OH:28])=[O:3])=[O:27])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3-{3-[3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-ureido}-propionic acid ethyl ester (prepared in Example 12B-c, 94 mg, 0.22 mmol) in ethanol (5 mL) at 25° C. was treated with a solution of potassium hydroxide (43 mg, 0.77 mmol) in water (1 mL). This solution was stirred at 25° C. for 2 h. At this time, the reaction was diluted with water (5 mL) and the ethanol was removed in vacuo. The aqueous layer was acidified to pH=2 with a 1N aqueous hydrochloric acid solution and extracted with methylene chloride (3×15 mL). The organic layers were then dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate plus 1% acetic acid) afforded 3-{3-[3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-ureido}-propionic acid (30 mg, 35%) as a white foam: FAB-HRMS m/e calcd for C18H22Cl2N2O4 (M+H)+401.1035, found 401.1022.

Workup

customthe ethanol was removed in vacuo
extractionextracted with methylene chloride (3×15 mL)
dry with materialThe organic layers were then dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e1329f93104e4317bc2042933c66321b
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528543B1

Reaction notes

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