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Example A: (R)-amino-cyclohexyl-acetic acid methyl ester hydrochloride <n="53"/>H-Cl H-ClTo a solution of acetyl chloride (0.5 mL, 7.04 mmol) in MeOH (10 rnL) at O0C is added (R)- amino-cyclohexyl-acetic acid hydrochloride (1.0 g, 5.16 mmol). The mixture is stirred at 6O0C for 16 hours. The reaction mixture is allowed to cool to room temperature and concentrated. The resulting residue is triturated with Et2O to afford the title compound (1.0 g, 93percent).
(2R)-cyclohexyl-[(N-[4-((2R,3R)-1-(4-fluorophenyl)-3-[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}glycyl)amino]acetic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
47%
Method 49; (2R)-cycloheXyl [(N-[4-((2R, 3R)-1-(4-fluorophenyl)-3-f [2-(4-fluorophenyl)-2- oxoethyl] thio}-4-oxoazetidin-2-yl) phenoxy] acetyl} glycyl) amino] acetic acid; TBTU (0. 0092 g, 0.029 mmol) was added to a mixture of 3- (R)-4- (R)-1- (4-Fluorophenyl)-3- [(4-fluorobenzoyl) methylthio]-4-{4-[N-(carboxymethyl) carbamoylmethoxy] phenyl} azetidin- 2-one (0.016g, 0.030 mmol) and N-methylmorpholin (0.101 ml, 0. 98 mmol) in DMF (2ml). The mixture was stirred overnight under N2-atmosphere. Additional TBTU (0.0092 g, 0.029 mmol) was added and the mixture was stirred at 35°C for 2 h. (2R)-amino (cyclohexyl) acetic acid hydrochloride (0.0068 g, 0.035 mmol) was added. The mixture was stirred at 35°C for 2 h and at room temperature overnight. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC on a Kromasil C8-column using a gradient of 5-100percent MeCN in 0.15percent trifluoroacetic acid buffer as eluent. The solvent was removed under reduced pressure and 0.009 g (47 percent) of the title product was obtained. M/z 680.01