Methanol → (2R)-2-amino-5-({2-[(carboxymethyl)amino]-1-[({3-{[4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxy-6-quinolinyl]amino}-1-[(dimethylamino)methyl]-3-oxopropyl}sulfanyl)methyl]-2-oxoethyl}amino)-5-oxopentanoic acid

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A mixture of 0.50 g (1.07 mmol) of 4-dimethylamino-but-2-enoic acid [4-(3-chloro-4-fluoro-phenylamino)-3-cyano-7-ethoxy-quinolin-6-yl]-amide, 0.328 g (1.07 mmol) of glutathione, and 0.2 mL of triethylamine in a solvent mixture consisting of 10 mL of methanol, 4 mL of water, and 4 mL of tetrahydrofuran was stirred for 7 h and then stored overnight in the refrigerator. The solvents were remove at reduced pressure at 30° C. Ethanol was added and removed three times giving 0.81 g of the title compound as a tan powder. A sample of this was purified by HPLC. The product was then isolated as the trifluoroacetate salt. Analysis for C34H40N8O8CIFS+(C2HF3O2)3; calcd: C, 43.00, H, 3.88, N, 10.03, Cl, 3.17; found: C, 42.23, H, 4.17, N, 10.03, Cl, 3.23.

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