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{4-[(S)-2-Acetylamino-2-(1-{(S)-2-carbamoyl-1-[3-(6-methoxy-naphthalen-1-yl)-propylcarbamoyl]-ethylcarbamoyl}-cyclohexylcarbamoyl)-ethyl]-benzyl}-phosphonic acid[ No CAS ]
{4-[(S)-2-Acetylamino-2-(1-{(S)-2-carbamoyl-1-[3-(6-methoxy-naphthalen-1-yl)-prop-2-ynylcarbamoyl]-ethylcarbamoyl}-cyclohexylcarbamoyl)-ethyl]-benzyl}-phosphonic acid di-tert-butyl ester[ No CAS ]
{4-[(S)-2-Acetylamino-2-(1-{(S)-2-carbamoyl-1-[3-(6-methoxy-naphthalen-1-yl)-propylcarbamoyl]-ethylcarbamoyl}-cyclohexylcarbamoyl)-ethyl]-benzyl}-phosphonic acid di-tert-butyl ester[ No CAS ]
3-methoxy-dinaphtho[2,1-<i>b</i>;2',3'-<i>d</i>]furan-8,13-quinone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
57%
In pyridine;
EXAMPLE 5 Preparation of 3-methoxydinaphtho-(2,1-b:2',3'-d)furan-8,13-dione Formula 30.19 g (0.133 mol) of 2,3-dichloro(1,4)-naphthoquinone and 23.14 g (0.133 mol) of <strong>[22604-07-5]6-methoxy-1-naphthol</strong> were dissolved in 400 ml of pyridine in a 1-liter three-necked flask. The solution was maintained at 85° C. with stirring for 18 hours. The reaction mixture was cooled to 5° C. and the solid was filtered off on a sinter funnel. The crystals were washed with water and then with methanol and diisopropyl ether and were dried. 24.8 g (yield: 57percent) of 3-methoxydinaphtho-(2,1-b:2',3'-d)furan-8,13-dione were obtained in the form of orange crystals. melting point: 292.1° C. (DSC) HPTLC: single spot 1H NMR (CDCl3): in agreement elemental analysis: UV-visible spectrum: CHCl3: lambdamax. nm (epsilon): 467.0 (104300), 319.0 (110500), 296.0 (430700), 284.5 (288400), 257.0 (596300), 230.5 (280400). X-ray diffraction spectrum
EXAMPLE 1 6-Methoxy-1-naphthalenol A mixture of 50.0 g (0.28 mole) of 6-methoxy-1-tetralone and 9.2 g (0.29 mole) of elemental sulfur was stirred and heated at 250°-260° for three hours (until the evolution of hydrogen sulfide gas had ceased). The mixture was cooled and then subjected to bulb-to-bulb distillation. The distillate was dissolved in 300 ml of dichloromethane, and the solution was extracted with 1.0N potassium hydroxide solution (3*150 ml). The base extracts were combined, cooled in ice, and acidified with 10percent hydrochloric acid to precipitate the crude naphthol product as a gum. Trituration of the gum with tert-butyl methyl ether yielded 16.8 g (34percent yield) of the analytically pure naphthol, mp 84°-86° (a mp of 83°-84° is given by M. P. Sibi, J. W. Dankwardt, and V. Snieckus, J. Org. Chem., 51, 271 (1986)). Calcd. for C11 H10 O2: C, 75.84; H, 5.79. Found C, 75.66; H, 5.69.
1-Hydroxy-6-methoxy-2-naphthalenecarboxylic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80%
In nitrogen; water; sodium hydrogencarbonate; N,N-dimethyl-formamide;
EXAMPLE 7 1-Hydroxy-6-methoxy-2-naphthalenecarboxylic acid A mixture of 14.0 g (0.080 mole) of <strong>[22604-07-5]6-methoxy-1-naphthalenol</strong> and 100 ml (0.25 mole) of a 2.5M solution of magnesium methyl carbonate in N,N-dimethylformamide were sealed in a 300 cc pressure reactor and pressurized to 550 psi with nitrogen gas. The reactor was heated to 180° for six hours without agitation, cooled, and then the reaction mixture was added to 1.75 kg of ice/water. The mixture was acidified with 6.0N aqueous hydrochloric acid. The precipitated crude product was filtered, stirred in 350 ml of fresh water, and re-filtered. The solid was dissolved with warming in 600 ml of 5percent aqueous sodium bicarbonate solution, and the solution was decolorized with activated charcoal. The filtrate from the charcoal treatment was cooled, washed with ethyl acetate (2*400 ml), cooled in ice, and again acidified with 6.0N aqueous hydrochloric acid. The precipitated product was filtered and washed with water to yield 14.0 g (80percent yield) of the analytically pure hydroxy acid, mp 188° dec. Calcd. for C12 H10 O4: C, 66.05; H, 4.62; Found: C, 66.36; H, 4.74.
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