benzyl (4R)-4,5-diamino-5-oxopentanoate;hydrochloride

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-(7-oxododecanoyl)-L-alanine (590 mg, 2.07 mmoles) and D-isoglutamine benzyl ester hydrochloride (565 mg, 2.07 mmoles) were dissolved in N,N-dimethylformamide (7 ml). The solution was cooled to 0° C. and diphenylphosphoryl azide (578 mg, 2.1 mmoles) and triethylamine (424 mg, 4.2 mmoles) were added thereto. The reaction mixture was stirred for 1 hour on an ice bath and for another 48 hours at room temperature. To the resulting suspension there were added benzene (5 ml) and ethyl acetate (25 ml) and it was washed successively with citric acid (0.52M; 3×5 ml), water (3×5 ml), saturated NaCl solution (3×5 ml), saturated NaHCO3 solution (3×5 ml), water (3×5 ml) and saturated NaCl solution (3×5 ml). The organic phase was dried with MgSO4 and filtered, the filtrate was evaporated and the compound was precipitated from n-hexane/diethyl ether. was washed successively with citric acid (0.52M; 3×5 ml), water (3×5 ml), saturated NaCl solution (3×5 ml), saturated NaHCO3 solution (3×5 ml), water (3×5 ml) and saturated NaCl solution (3×5 ml) The organic phase was dried with MgSO4 filtered the filtrate was evaporated the compound was precipitated from n-hexane/diethyl ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 3.36 of benzyl t-butyloxycarbonyl-D-isoglutaminate (4, n = 2) there is added 50 ml of a saturated solution of hydrogen chloride in ethyl acetate. The reaction mixture is stored at 22° C for 10 minutes and then 75 ml of ether is added to precipitate the product, which is collected by centrifugation and carefully dried in vacuo to give benzyl D-isoglutaminate hydrochloride (5, n = 2) which is used without further purification in step B of this example. to precipitate the product, which is collected by centrifugation carefully dried in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-(7-oxododecanoyl)-L-alanine (590 mg, 2.07 mmoles) and D-isoglutamine benzyl ester hydrochloride (565 mg, 2.07 mmoles) were dissolved in N,N-dimethylformamide (7 ml). The solution was cooled to 0° C. and diphenylphosphoryl azide (578 mg, 2.1 mmoles) and triethylamine (424 mg, 4.2 mmoles) were added thereto. The reaction mixture was stirred for 1 hour on an ice bath and for another 48 hours at room temperature. To the resulting suspension there were added benzene (5 ml) and ethyl acetate (25 ml) and it was washed successively with citric acid (0.52M; 3×5 ml), water (3×5 ml), saturated NaCl solution (3×5 ml), saturated NaHCO3 solution (3×5 ml), water (3×5 ml) and saturated NaCl solution (3×5 ml). The organic phase was dried with MgSO4 and filtered, the filtrate was evaporated and the compound was precipitated from n-hexane/diethyl ether. was washed successively with citric acid (0.52M; 3×5 ml), water (3×5 ml), saturated NaCl solution (3×5 ml), saturated NaHCO3 solution (3×5 ml), water (3×5 ml) and saturated NaCl solution (3×5 ml) The organic phase was dried with MgSO4 filtered the filtrate was evaporated the compound was precipitated from n-hexane/diethyl ether