9-氨基芴

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 18.1 g of 9-aminofluorene are reacted with epichlorohydrin, following the procedure described in Example 47, to give 1-(9-fluorenylamino)-2-hydroxy-3-chloropropane, from which, without purification, (9-fluorenylaminomethyl)oxirane is obtained with methanolic sodium hydroxide solution, by the procedure described in Example 48. Reaction of this compound with 17.8 g of 4-trans-propenylguaethol gives 16.1g = 38.7% of theory of 1-(2-ethoxy-5-trans-propenyl-phenoxy)-2-hydroxy-3-(9-fluorenylamino)-propane, which crystallizes out from the reaction solution in the cold in the form of the free base. Colorless crystals which have a melting point of 119°-121° and are identical to the product described in Example 28.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A DMF (2 mL) solution of [3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]propiolic acid (74 mg) and 9-aminofluorene (65 mg) and BOP (133 mg) and N,N′-IPEA (77 μL) was agitated at room temperature overnight. Water and chloroform were added to the reaction solution, the organic layer was partitioned and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Carrier: Chromatorex NH, elution solvent: heptane-ethyl acetate system), and 45 mg of the title compound was obtained. the organic layer was partitioned concentrated under reduced pressure The residue was purified by silica gel column chromatography (Carrier: Chromatorex NH, elution solvent: heptane-ethyl acetate system)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A DMF (2 mL) solution of [3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]propiolic acid (74 mg) and 9-aminofluorene (65 mg) and BOP (133 mg) and N,N′-IPEA (77 μL) was agitated at room temperature overnight. Water and chloroform were added to the reaction solution, the organic layer was partitioned and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Carrier: Chromatorex NH, elution solvent: heptane-ethyl acetate system), and 45 mg of the title compound was obtained. the organic layer was partitioned concentrated under reduced pressure The residue was purified by silica gel column chromatography (Carrier: Chromatorex NH, elution solvent: heptane-ethyl acetate system)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A DMF (2 mL) solution of [3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]propiolic acid (74 mg) and 9-aminofluorene (65 mg) and BOP (133 mg) and N,N′-IPEA (77 μL) was agitated at room temperature overnight. Water and chloroform were added to the reaction solution, the organic layer was partitioned and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Carrier: Chromatorex NH, elution solvent: heptane-ethyl acetate system), and 45 mg of the title compound was obtained. the organic layer was partitioned concentrated under reduced pressure The residue was purified by silica gel column chromatography (Carrier: Chromatorex NH, elution solvent: heptane-ethyl acetate system)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: DMF was added to a stirred suspension of 4-benzoyloxy-5-methoxy-2-nitro benzoic acid (6) (0.500 mg, 1.65 mmol) and thionyl chloride (3 ml) in dry benzene (30 ml) and the stirring was continued for 6 h. The benzene was evaporated in vacuum and the resultant oil dissolved in dry THF (50 ml) and added dropwise over a period of 1 h to a stirred suspension of 9H-9-fluorenamine (326, 15.6 mmol) triethylamine (5 ml). After the completion of addition, the reaction mixture was brought to ambient temperature and stirred for an additional hour. The THF was evaporated in vacuum and the aqueous layer was washed with ethyl acetate. The aqueous phase was then adjusted to pH 3 using 6 N HCl and extracted with ethyl acetate and washed with brine, dried over Na2SO4 and evaporated in vacuum to afford the crude product of (7e) (620 mg in 80% yield). 1H NMR (CDCl3) δ 3.95 (s, 3H), 5.20 (s, 2H), 5.70 (s, 1H), 6.70 (s, 1H), 7.00-7.41 (m, 5H), 7.45-7.706 (m, 9H); FABMS: 466 (M+H)+. The benzene was evaporated in vacuum the resultant oil dissolved in dry THF (50 ml) After the completion of addition was brought to ambient temperature The THF was evaporated in vacuum the aqueous layer was washed with ethyl acetate extracted with ethyl acetate washed with brine dried over Na2SO4 evaporated in vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 1.0 ml of ethyl acrylate was added to a solution of 9-aminofluorene (1.24 g) in ethanol (20 ml). The resultant mixture was stirred at 80° C. for 5 hours and, then, at room temperature for 36 hours. The residue obtained by condensing the reaction mixture was dissolved in methylene chloride and, then, washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by a silica gel column chromatography (eluting solution: methylene chloride-ether) to give 1.25 g of N-(9-fluorenyl)-β-alanine ethyl ester. The residue obtained by condensing the reaction mixture washed with saturated saline dried over anhydrous magnesium sulfate concentrated The residue was purified by a silica gel column chromatography (eluting solution: methylene chloride-ether)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 3-Methyl-7β-phenoxyacetamidoceph-3-em-4-carboxylic acid (3.48 g., 10 m. moles) was dissolved with 9-aminofluorene (17.5 m moles) in dichloromethane (50 ml) together with isobutyl nitrite (3.62 g., 35 m. moles) and warmed at 35° for 18 hours. The reaction mixture was worked up as described in Example 7 except that a small quantity of ester (0.24, 0.48 m. moles) was filtered from the solution after the acid aqueous wash. On removal of the solvent the crystalline ester was slurried with warm isopropanol (50 ml), cooled and filtered to give the previously unreported title compound (2.60 g) m.pt. 214°, pure by t.l.c. Together with the previously filtered solid the weight of ester isolated represents a 56.8% yield based on the input acid. An analytical sample of the ester crystallised from acetone-methanol had m.pt. 221° - 222.5°; ν max (1% CHBr3 solution) 3390 (--NHCO--), 1778 (β-lactam) 1718 (αβ-unsaturated ester), 1688 + 1520 cm-1 (amide carbonyl); τ (8% CDCl3 solution) 2.2 - 3.2 (complex, phenoxy ring + (--NHCO--) + fluorenyl 9-C + fluorenyl ring), 5.47 (singlet, phenoxy methylene acetamido group, H2), 4.20 (doublet of doublets, J 10, 5 Hz, C-7, H), 5.04 (doublet, J 5 Hz, C-6, H), 6.45 + 6.89 (two doublets [branches of a quartet], J 18 Hz, H2), 7.84 (singlet, C-3, H3). Found C, 67.68; H, 4.64; N, 5.47. C29H24N2O5S requires C, 67.97; H, 4.72; N, 5.47%. warmed at 35° for 18 hours was filtered from the solution after the acid aqueous wash On removal of the solvent the crystalline ester cooled filtered

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A DMF (2 mL) solution of [3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]propiolic acid (74 mg) and 9-aminofluorene (65 mg) and BOP (133 mg) and N,N′-IPEA (77 μL) was agitated at room temperature overnight. Water and chloroform were added to the reaction solution, the organic layer was partitioned and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Carrier: Chromatorex NH, elution solvent:heptane-ethyl acetate system), and 45 mg of the title compound was obtained. the organic layer was partitioned concentrated under reduced pressure The residue was purified by silica gel column chromatography (Carrier: Chromatorex NH, elution solvent:heptane-ethyl acetate system)