Hydrochloric Acid → HCID 136347958, compound

HRID 1618024Notes

Reaction equation

C([O:3][C:4](=[O:36])[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])[CH2:18]/[C:19](=[N:27]\[OH:28])/[C:20]3[CH:25]=[CH:24][N:23]=[C:22]([CH3:26])[CH:21]=3)=[CH:13][CH:12]=2)[N:8]=[N:7]1)C.[OH-].[Li+].Cl>O1CCOCC1.O>[OH:28]/[N:27]=[C:19](/[C:20]1[CH:25]=[CH:24][N:23]=[C:22]([CH3:26])[CH:21]=1)\[CH2:18][CH:17]([C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:8]=[N:7][N:6]([CH2:5][C:4]([OH:36])=[O:3])[CH:10]=2)=[CH:12][CH:13]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH3:35]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of (4-{4-[(−)-3-[(E)-hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-phenyl}-[1,2,3]triazol-1-yl)-acetic acid ethyl ester (35 mg) in a mixture of dioxane (1 mL) and water (1 mL) was added lithium hydroxide (14 mg) and the reaction mixture heated by microwave irradiation to 120° C. for 20 min. The solution was adjusted to approximately pH 3 by using 1 M aqueous hydrochloric acid and then extracted over a sat. solution of brine (50 mL) with ethyl acetate (3×50 mL). The combined organic phases were dried over sodium sulfate and the crude reaction product purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of dichloromethane/methanol (100:0 to 90:10). Light yellow solid. MS (ESI−): m/z=454.1 ([M−H]−).

Workup

extractionextracted over a sat. solution of brine (50 mL) with ethyl acetate (3×50 mL)
dry with materialThe combined organic phases were dried over sodium sulfate
customthe crude reaction product
custompurified by silica gel chromatography
washeluting with a gradient of dichloromethane/methanol (100:0 to 90:10)

Sources & evidence

ORD record: ord-57a80b241d864f80b34669fb1cf4335a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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