Hydrochloric Acid → HCID 67705253, compound

Participants

Reaction Conditions

Reaction Steps

Add 1M aqueous lithium hydroxide (4.0 mL, 4.0 mmol) to a solution of diethyl (1S,2R,3R,4S,5R,6S)-4-[(2-acetoxyacetyl)amino]-2-(tert-butoxycarbonylamino)-3-[(3,4-dichlorophenyl)methoxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate (0.42 g, 0.67 mmol) in tetrahydrofuran (7.0 mL) at room temperature and stir overnight. Acidify the reaction to approximately pH 1 with 5N aqueous HCl. Extract with ethyl acetate (3×25 mL). Dry the combined organic layers, filter, and conc. under reduced pressure. HPLC analysis of crude reaction mixture shows starting material present. Add a 1M aqueous lithium hydroxide (4.0 mL, 4.0 mmol) to a solution of the crude reaction mixture in tetrahydrofuran (7.0 mL) and heat at 50° C. After 17 hours, acidify reaction to approximately pH 1 with 5N aqueous HCl. Extract with ethyl acetate (3×25 mL). Dry the combined extracts, filter, and conc. under reduced pressure. Purify by preparative reverse-phase high performance liquid chromatography using a gradient of 95% water (with 0.03% HCl)/5% acetonitrile to 5% water (with 0.03% HCl)/95% acetonitrile over 40 min. to provide (1S,2R,3R,4S,5R,6S)-2-(tert-butoxycarbonylamino)-3-[(3,4-dichlorophenyl)methoxy]-4-[(2-hydroxyacetyl)amino]bicyclo[3.1.0]hexane-2,6-dicarboxylic acid (0.181 g, 0.34 mmol, 51%) as a white solid. MS (m/z): 531 (M−H).

Provenance & Evidence