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ChemicalBook CAS DataBase List Z-PRO-GLY-NH2
35010-96-9

Z-PRO-GLY-NH2 synthesis

3synthesis methods
-

Yield:35010-96-9 100%

Reaction Conditions:

with dmap;1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane at 20;

Steps:

1

1-{[(Phenylmethyl)oxy]carbonyl}-L-proline (8.79 mmol, 2.19 g), glycinamide hydrochloride (8.79 mmol, 0.97 g), DMAP (26.38 mmol, 3.22 g), and EDCI (13.19 mmol, 2.54 g) were all dissolved in CH2Cb (80 ml_) at room temperature and stirred overnight. An additional 100 ml_ CH2CI2 was added, followed by 1 N HCI (100 ml_). The organic layer was separated, dried (Na2SO4), filtered, and evaporated to give the desired product as a white solid in quantitative yield.PIFA (4.85 mmol, 2.09 g) was dissolved in CH3CN (15 mL) and diluted with H2O (15 ml_). 1-{[(Phenylmethyl)oxy]carbonyl}-L-prolylglycinamide (4.8 mmol, 1.48 g) was added to this solution and the reaction mixture was stirred at room temperature overnight. It was then diluted with 1 N HCI (150 mL) and washed twice with diethyl ether. The aqueous layer was concentrated in vacuo to give the desired product in quantitative yield. The resulting white solid was used without further purification.Phenylmethyl (2S)-2-{[(aminomethyl)amino]carbonyl}-1-pyrrolidinecarboxylate hydrochloride (0.988 mmol, 0.312 g), 2-pyridinecarboxylic acid (0.988 mmol, 0.122 g), HOAT (1.186 mmol, 0.161 g), EDCI (1.186 mmol, 0.228 g), and NMM (9.88 mmol, 1.1 mL) were all dissolved in DMF (10 mL) and stirred at room temperature overnight. The crude reaction was purified by reverse phase HPLC to give a yellow oil (0.25 g, 66% yield). Phenylmethyl (2S)-2-[({[(2-pyridinylcarbonyl)amino]methyl}amino)carbonyl]-1- pyrrolidinecarboxylate (0.654 mmol, 0.25 g) was dissolved in methanol (15 mL) and hydrogenated at atmospheric pressure in the presence of 10% Pd on C (50 mg). After stirring 3 hours, the suspension was filtered and concentrated in vacuo. The product was obtained as a colorless oil (0.154 g, 95% yield) which solidified on standing.λ/-[(L-Prolylamino)methyl]-2-pyridinecarboxamide (0.605 mmol, 150 mg) and (2R)-3- cyclopentyl^-^formyl^phenylmethy^oxylaminoImethyOpropanoic acid (0.605 mmol, 184 mg) were dissolved together in DMF (6 mL). NMM (3.025 mmol, 0.33 mL) was added, followed by HOAT (0.726 mmol, 99 mg) and EDCI (0.726 mmol, 140 mg). The reaction mixture was stirred at room temperature overnight before being filtered and purified by reverse phase HPLC. The desired product was obtained in 31 % yield (101 mg).A/-[({1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-L- prolyl}amino)methyl]-2-pyridinecarboxamide (0.189 mmol, 0.101 g) was dissolved in methanol (10 mL) and hydrogenated at atmospheric pressure in the presence of 10% Pd on C (20 mg). After stirring overnight, the reaction mixture was filtered and concentrated. The title compound was obtained cleanly in greater than 90% yield. LC-MS m/z 446 (MH+)

References:

WO2007/67906,2007,A2 Location in patent:Page/Page column 24-25

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