| 90% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 48h;Product distribution / selectivity; |
[00166] 9. 4- (4-Ethyl-3,13-dioxo-3,4,12,13-tetrahydro-lfl-2-oxa- 6, 12a-diaza-dibenzo [b,h] fluoren-4-yloxycarbonylmethoxy) -benzoic acid-10 , 13-dimethyl-17-oxo-hexadecahydro-cyclopenta [a] phenanthren- 3-yl ester (OLl); .Reactions :(f) CPT-phenoxyacetic acid: A mixture of camptothecin (100 mg, 0.29 mmol) , <strong>[19360-67-9]4-carboxyphenoxyacetic acid</strong> (112 mg, 0.57 mmol) , EDCI(82 mg, 0.43 mmol), DMAP (10 mg, 0.10 mmol), and DMF/DCM (4 mL/4 mL) was stirred at ambient temperature for 48 hr . The resulting solution was then diluted by adding dichloromethane (50 mL) . The dichloromethane containing organic layer was washed sequentially with a saturated NH4C1 solution (20 mL) , water (20 mL) , and brine(20 mL) . After drying over MgS04, the solvent was removed under in vacuo. The resulting residue was then purified by flash column chromatography (chloroform/methanol (20:1) to afford CPT- phenoxyacetic acid as a light yellow solid (129 mg; yield = 90%) . |
| 67% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 48h; |
The mixture of camptothecin (100 mg, 0.287 mmol), <strong>[19360-67-9]4-carboxyphenoxyacetic acid</strong> (1.12 mg, 0.57 mmol), EDCI (82 mg, 0,43 mmol), DMAP (10 mg, 0.1 mmol), N,N-dimethylformamide (4 ml) and dichloromethane (4 ml) were stirred in the room temperature for 48 h, then dichloromethane (50 ml) was added to the solution. Organic layer was washed with water (20 ml), saturated NaHCO3 aqueous solution (20 ml) and brine (20 ml), and then dried over MgSO4. After the solvent was removed under reduced pressure, the resulting solid was separated by column chromatography (eluent: CHCl3: C2H5OH 5:1) to afford 80 mg camptothecin-20-O-4-fluorophenoxyacetate, yield: 67.0%, mp (dec).The chemical structure analysis was performed by 1HNMR (CDCl3, 600 MHz): delta 8.40 (s, 1H, Ar-H), 8.30 (d, 1H, Ar-H), 8.07 (m, 2H, Ar-H), 7.95 (d, 1H, Ar-H), 7.86 (t, 1H, Ar-H), 7.67 (t, 1H, Ar-H), 7.25 (s, 1H, Ar-H), 6.96 (m, 2H, Ar-H), 5.68 (d, 1H, H17), 5.43 (d, 1H, H17), 5.29 (s, 2H, H5), 4.91 (q, 2H, OCH2CO), 2.25 (dm, 2H, CH2), 0.97 (t, 3H, CH3). |
| 59.6% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); dichloromethane; at 20℃; for 20h; |
The mixture of camptothecin (30 mg, 0.086 mmol), <strong>[19360-67-9]4-carboxyphenoxyacetic acid</strong> (40 mg, 0.20 mmol), EDCI (65 mg, 0.34 mmol), DMAP (2 mg, 0.02 mmol), dichloromethane (2 ml) and DMF (2 ml) was stirred in the room temperature for 20 h, then dichloromethane (20 ml) was added to the solution. Organic layer was washed with water (20 ml) and brine (20 ml), and then dried over MgSO4. After the solvent was removed under reduced pressure, the resulting solid was separated by column chromatography (eluent: CHCl3:CH3OH 7:3) to afford 27 mg camptothecin-20-O-4-carboxyphenoxyacetate, yield: 59.6%, mp 243-245 C. (dec.). The chemical structure analysis was performed by 1HNMR (CDCl3, 600 MHz): delta 8.41 (s, 1H, Ar-H), 8.29 (d, 1H, Ar-H), 8.03 (d, 2H, Ar-H), 7.96 (d, 1H, Ar-H), 7.86 (s, 1H, Ar-H), 7.68 (s, 1H, Ar-H), 7.23 (s, 1H, Ar-H), 6.98 (d, 2H, Ar-H), 5.69 (d, 1H, H17), 5.41 (d, 1H, H17), 5.31 (q, 2H, H5), 4.92 (q, 2H, OCH2CO), 2.23 (d, 2H, CH2), 0.98 (s, 3H, CH3). |
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