Hydrochloric Acid → HCID 67549360, compound

HRID 43520Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@@H:12]2[CH2:17][CH2:16][N:15]([C:18]3[S:19][C:20]([C:24](O)=O)=[C:21](C)[N:22]=3)[CH2:14][C@@H:13]2[O:27][CH3:28])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].Cl.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@@H:12]2[CH2:17][CH2:16][N:15]([C:18]3[S:19][C:20]([CH3:24])=[CH:21][N:22]=3)[CH2:14][C@@H:13]2[O:27][CH3:28])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

Conditions

Temperature: 60 °C

Procedure

2-[(3S,4R)-4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylic acid obtained by the method described in Example (56d) (15 mg, 0.035 mmol) was dissolved in THF (3 mL). 1 N hydrochloric acid (1 mL) was added, and the mixture was stirred at 60° C. for 40 minutes. A 1 N aqueous sodium hydroxide solution was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with brine and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=1/1, ethyl acetate) to obtain 13.5 mg of the title compound as a white solid (100%).

Workup

extractionfollowed by extraction with ethyl acetate
washThen, the organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentration under reduced pressure
customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=1/1, ethyl acetate)

Sources & evidence

ORD record: ord-ea92617443dc4dbd89122b178809b605
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536197B2

Reaction notes

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