Hydrochloric Acid → 3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-3H-imidazole-4-carboxylic acid

HRID 900232Notes

Reaction equation

C[O:2][C:3]([C:5]1[N:6]([CH2:10][C:11]2[CH:15]=[C:14]([C:16]3[S:17][C:18]([Cl:21])=[CH:19][CH:20]=3)[O:13][N:12]=2)[CH:7]=[N:8][CH:9]=1)=[O:4].O.[OH-].[Li+].Cl>C1COCC1.O>[Cl:21][C:18]1[S:17][C:16]([C:14]2[O:13][N:12]=[C:11]([CH2:10][N:6]3[C:5]([C:3]([OH:4])=[O:2])=[CH:9][N:8]=[CH:7]3)[CH:15]=2)=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 720 mg 3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-3H-imidazole-4-carboxylic acid methyl ester in 10 ml THF and 3 ml water, 57.0 mg lithium hydroxide monohydrate were added. After stirring for 2 h at 60° C. the reaction was cooled to RT. The mixture was acidified with half concentrated hydrochloric acid and the precipitate collected by filtration and washed with 3 ml water. The product was obtained as a white solid which was dried under reduced pressure. Yield: 650 mg

Workup

temperaturewas cooled to RT
filtrationthe precipitate collected by filtration
washwashed with 3 ml water
customThe product was obtained as a white solid which
customwas dried under reduced pressure

Sources & evidence

ORD record: ord-b4682ecc42c9478b82e8da74ffb67ad0
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07358268B2

Reaction notes

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