Hydrochloric Acid → 2-(S)-(benzooxazol-2-ylamino)-3-cyclohexyl propionic acid
Reaction equation
[CH2:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C@H:8]([NH2:12])[C:9]([OH:11])=[O:10])[CH2:3][CH2:2]1.[OH-].[Na+].Cl[C:16]1[O:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1.Cl>CS(C)=O>[O:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[NH:12][C@@H:8]([CH2:7][CH:4]1[CH2:3][CH2:2][CH2:1][CH2:6][CH2:5]1)[C:9]([OH:11])=[O:10]Participants
Procedure
A slurry of L-cyclohexylalanine (2.44 g, 14.3 mmol) and powdered NaOH (1.14 g, 28.6 mmol) in DMSO (20 mL) was heated to 100° C. for 20 min until the mixture viscosity decreased and stirring was enabled. 2-Chlorobenzoxazole (1.99 g, 13.0 mmol) was added, and the solution was stirred at 100° C. for 4 h. Upon cooling to room temperature, the solution was poured into 1 M HCl. The precipitate was filtered and dried to afford 2-(S)-(benzooxazol-2-ylamino)-3-cyclohexyl propionic acid was isolated as a white powder (1.69 g, 41%). Step B. To a stirring solution of 2-(S)-(benzooxazol-2-ylamino)-3-cyclohexyl propionic acid (288 mg, 1.0 mmol), N1-(4-methoxy-phenyl)-ethane-1,2-diamine.2HCl (239 mg, 1.0 mmol), and iPr2NEt (0.87 mL, 5.0 mmol) in dichloromethane (4 mL) was added HATU (418 mg, 1.1 mmol). The solution was stirred at room temperature for 4 hours and then evaporated to dryness. The crude material was chromatographed over silica gel (Hexanes/EtOAc) to afford the title compound as a white powder (243 mg, 56%). HPLC-MS calcd. for C25H32N4O3 (M+H+) 437.25. found 437.5.
Workup
- stirringthe solution was stirred at 100° C. for 4 h
- filtrationThe precipitate was filtered
- customdried
Sources & evidence
- ORD record
- ord-6324935dc4974fcb82be295325c40dc4
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07173051B2
Reaction notes
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