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With phosphorus pentachloride; hydrogen bromide; potassium hydrogencarbonate; In chloroform; water; acetic acid;
b. 84 g. of N-benzyloxycarbonylglycine were suspended in 500 ml. of alcohol-free chloroform and the suspension was cooled to -20° C. The stirred suspension was treated portionwise over a period of 15 minutes with 90 g. of phosphorus pentachloride and the stirring was continued until a clear solution was obtained. At this point, the cold mixture was added dropwise over a period of 30 minutes to a cold (-5° C.) vigorously stirred emulsion consisting of 82 g. of 5-chloro-2-methyl-aminobenzophenone, 347 g. of potassium bicarbonate, 700 ml. of chloroform and 1400 ml. of water. The resulting mixture was stirred for a further 1 hour at -5° C. and then overnight at room temperature. The stirring was then discontinued and the liquid phases allowed to separate. The chloroform layer was washed three times with 500 ml. of water each time and evaporated in vacuo to give 150.7 g. of a viscous yellow gum which was shown by physical methods to be almost pure (above 95percent) 2-(N-benzyloxycarbonylamino)-N-(2-benzoyl-4 -chlorophenyl)-N-methylacetamide. The product obtained according to the preceding paragraph was dissolved in 650 ml of a 30percent solution of hydrogen bromide in glacial acetic acid and treated in an identical manner to that described in part (a) of this Example to give 2-amino-N-(2-benzoyl-4-chlorophenyl)-N-methylacetamide hydrobromide in a 77percent overall yield from 5-chloro-2-methylaminobenzophenone.
Step a) Synthesis of Z-Gly-Pro tert-Butyl EsterA solution of Z-Gly (1 .087 g, 5.2 mmol), and N-methylmorpholine (0.571 mL, 5.2 mmol) in THF (15mL), was cooled to -15C, and treated with isobutyl chloroformate (0.679 mL, 5.2 mmol). After stirring for 10 min at -15C, the mixture was treated with L-proline t-butyl ester-HCI (0.831 g, 4.0 mmol), and N- methylmorpholine (0.571 mL, 5.2 mmol). Work-up: the reaction mixture was diluted with ethyl acetate (50 mL), washed with 1 N HCL, 1 N NaHC03, and brine, then dried with anhydrous Na2S04. This solution was filtered and concentrated to give 1 .45 g of a white solid. This material was used in the next step without further purification.
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