Potassium Hydroxide → HCID 22389490, compound

HRID 1860160Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of {3-[3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-ureido}-acetic acid ethyl ester (prepared in Example 12B-d, 77 mg, 0.19 mmol) in ethanol (5 mL) at 25° C. was treated with a solution of potassium hydroxide (36 mg, 0.65 mmol) in water (1 mL). The reaction mixture 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 then acidified to pH=2 with a 1N aqueous hydrochloric acid solution and extracted with methylene chloride (3×15 mL). The organics were then dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 88/12 chloroform/methanol plus 1% acetic acid) afforded {3-[3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-ureido}-acetic acid (43 mg, 60%) as a white solid: mp 204.2-206.8° C.; EI-HRMS m/e calcd for C17H20Cl2N2O4 (M+) 386.0800, found 386.0795.

Workup

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

Sources & evidence

ORD record: ord-841194a0c5084c3a961be37b91e1e52b
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528543B1

Reaction notes

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