[CH3:1][C:2]1([O:6][C:7]([NH:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:8])[CH2:5][CH2:4][CH2:3]1.Cl.[CH3:22][O:23][C:24](=[O:28])[C@H:25]([CH3:27])[NH2:26].C(Cl)Cl>C(N(CC)CC)C>[CH3:1][C:2]1([O:6][C:7]([NH:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:8])[CH2:3][CH2:4][CH2:5]1.[CH3:22][O:23][C:24](=[O:28])[C@H:25]([CH3:27])[NH2:26]A solution of 0.67 mM of the hydroxysuccinimide ester of N-(1-methylcyclobutyloxycarbonyl) phenylalanine and 0.70 mM of alanine methyl ester hydrochloride in 10 ml. of methylene chloride is treated with triethylamine until the pH is adjusted to 7.6-8.0. Reaction is stirred 6 hours and the reaction mixture is washed according to the following procedure: one time with dilute sodium bicarbonate solution; once with 50% saturated sodium chloride solution; once with 0.2 N sulfuric acid saturated with sodium sulfate; and two times with 50% saturated sodium chloride solution. The resulting material is dried over sodium sulfate and the washing procedure repeated. The solvent is removed in vacuo to afford N-(1-methylcyclobutyloxycarbonyl) phenylalanine-alanine methyl ester.
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