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CAS No. : | 196404-55-4 | MDL No. : | MFCD09837613 |
Formula : | C22H25NO6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MSVWUXLRSKRKFZ-PAMZHZACSA-N |
M.W : | 399.44 | Pubchem ID : | 11165464 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67.9% | With hydrogen; palladium(II) hydroxide In methanol at 20℃; for 1 h; | 10141] The product obtained in the previous step (4.83 g,9.88 mmol) was dissolved in 10 ml of methanol, into which1.0 g of palladium hydroxide was added. Hydrogen wasintroduced (20 psi) at room temperature and reacted forabout 1 h, the completion of the reaction was monitored by TLC. The reaction liquid was filtered, concentrated, separated and purified by column chromatography (petroleum ether/ethyl acetate=5:1), to give the final product as a white solid (2.68 g, 67.9percent). |
67.9% | With hydrogen; palladium(II) hydroxide In methanol at 20℃; for 1 h; | h. Preparation of (4S,5R)-3-t-butoxy carbonyl-2-(4-methoxyphenyl)-4-phenyl-5-oxazolidine carboxylic acid (0164) methanol, into which 1.0 g of palladium hydroxide was added. Hydrogen was introduced (20 psi) at room temperature and reacted for about 1 h, the completion of the reaction was monitored by TLC. The reaction liquid was filtered, concentrated, separated and purified by column chromatography (petroleum ether/ethyl acetate=5:1), to give the final product as a white solid (2.68 g, 67.9percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | at 20℃; | The above mention product 7 dissolved with ΜeOΗ, added dilute NaOH and stir at room temperature, TLC has been monitored after completion of the reaction and remove MeOH, the residue is diluted with Ac0Et / H20, static stratification. Into the aqueous phase added the AcOEt, and adjust the pH with dilute hydrochloric acid. The mixture is allowed to stand for separation, the organic phase has been separated, and the aqueous phase has been extracted with AcOEt, the combined organic phases are washed with water, dried over anhydrous MgS04, the solvent has been removed, and then obtained benzooxazoline carboxylic acid 8, yield of both steps is 92percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With methanol; sodium hydroxide; at 20℃; | The above mention product 7 dissolved with MueOEta, added dilute NaOH and stir at room temperature, TLC has been monitored after completion of the reaction and remove MeOH, the residue is diluted with Ac0Et / H20, static stratification. Into the aqueous phase added the AcOEt, and adjust the pH with dilute hydrochloric acid. The mixture is allowed to stand for separation, the organic phase has been separated, and the aqueous phase has been extracted with AcOEt, the combined organic phases are washed with water, dried over anhydrous MgS04, the solvent has been removed, and then obtained benzooxazoline carboxylic acid 8, yield of both steps is 92%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 12.0h;Inert atmosphere; | To the solution of oxazolidine-type protected N-tert-butoxycarbonylphenylisoserine (0.056 g, 0.140 mmol) and 2 (0.065 g, 0.117 mmol) in dry CH2Cl2 (Ar-atmosphere) were added N,N?-dicyclohexylcarbodiimide DCC (0.044 g, 0.210 mmol) and 4-(dimethylamino)pyridine DMAP (0.02 g). The reaction mixture was stirred at room temperature. In 12 h one drop of acetic acid was added and after 15 min the solvent was evaporated, the residue was dissolved in ethyl acetate and kept at 4C for 8-12 h. The sediment was filtered and filtrate was washed with 0.1N HCl, water, dried over MgSO4 and evaporated. Chromatographic purification (ethyl acetate/petroleum ether 1:4) gave 3 as yellowish powder (0.077 g, yield 73%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67.9% | With hydrogen; palladium(II) hydroxide; In methanol; at 20℃; under 103.432 Torr; for 1.0h; | 10141] The product obtained in the previous step (4.83 g,9.88 mmol) was dissolved in 10 ml of methanol, into which1.0 g of palladium hydroxide was added. Hydrogen wasintroduced (20 psi) at room temperature and reacted forabout 1 h, the completion of the reaction was monitored by TLC. The reaction liquid was filtered, concentrated, separated and purified by column chromatography (petroleum ether/ethyl acetate=5:1), to give the final product as a white solid (2.68 g, 67.9%). |
67.9% | With hydrogen; palladium(II) hydroxide; In methanol; at 20℃; under 1034.32 Torr; for 1.0h; | h. Preparation of (4S,5R)-3-t-butoxy carbonyl-2-(4-methoxyphenyl)-4-phenyl-5-oxazolidine carboxylic acid (0164) methanol, into which 1.0 g of palladium hydroxide was added. Hydrogen was introduced (20 psi) at room temperature and reacted for about 1 h, the completion of the reaction was monitored by TLC. The reaction liquid was filtered, concentrated, separated and purified by column chromatography (petroleum ether/ethyl acetate=5:1), to give the final product as a white solid (2.68 g, 67.9%). |
With hydrogen; palladium(II) hydroxide; In methanol; at 20℃; under 1034.32 Torr; for 1.0h;Inert atmosphere; | General procedure: A typical procedure is given for the preparation of (4S,5R)-N-butyloxycarboryl-2-(4-anisyl)-4-isobutyl-5-oxazolidine carboxylic acid 7d: To a mixture of compound 6 (15.60 g, 33.20 mmol) in MeOH (400 mL) was added Pd(OH)2 (7.80 g). The reaction was stirred at room temperature under H2 atmosphere (20 psi) for 1 h. TLC showed the reaction was complete. The resulting mixture was filtered, and the filtrated was concentrated. The residue was purified by column chromatography (Petroleum ether/EtOAc = 10:1, 5:1) togive 7d (10.98 g, yield 87.2%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: A solution of 4 equiv 7a in dry CH2Cl2, was added with 1 equiv baccatin derivative, 2 equiv DCC, 0.5 equiv DMAP and 0.2 equiv PTSA, at room temperature with stirring overnight. The reaction was evaporated under reduced pressure. Chromatography of the crude mixture (n-hexane/EtOAc = 2:1) afforded 16 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: A solution of 4 equiv 7a in dry CH2Cl2, was added with 1 equiv baccatin derivative, 2 equiv DCC, 0.5 equiv DMAP and 0.2 equiv PTSA, at room temperature with stirring overnight. The reaction was evaporated under reduced pressure. Chromatography of the crude mixture (n-hexane/EtOAc = 2:1) afforded 16 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; | 3) Preparation of PCMI-22 (0172) 10-Dimethylcarbamoyl-7-methoxy baccatin III (1 eq.) and (4S,5R)-3-t-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-5-oxazolidine carboxylic acid (4 eq.) were dissolved in dichloromethane at room temperature, into which 0.5 equivalents of 4-dimethylaminopyridine (DMAP) and 2.0 equivalents of N,N-dicyclohexylcarbodiimide (DCC) were successively added and reacted overnight. The obtained product was reacted in 2 equivalents of acetyl chloride/methanol solution to give the final taxane derivative PCMI-22. The overall yield of the two steps was 71% and the purity of the product was 95% or higher. (0173) PCMI-22: mp: 239-240 C.; (0174) MS (m/z) ESI: 915.3 (M+Na)+; (0175) 1H NMR (400 MHz, CDCl3) delta 8.11 (d, J=7.4 Hz, 2H), 7.62 (t, J=7.4 Hz, 1H), 7.50 (t, J=7.7 Hz, 2H), 7.44-7.30 (m, 5H), 6.42 (s, 1H), 6.21 (t, J=8.6 Hz, 1H), 5.67 (d, J=6.9 Hz, 1H), 5.50 (d, J=8.3 Hz, 1H), 5.28 (d, J=8.3 Hz, 1H), 4.98 (d, J=8.2 Hz, 1H), 4.64 (s, 1H), 4.31 (d, J=8.6 Hz, 1H), 4.18 (d, J=8.4 Hz, 1H), 3.92-3.82 (m, 2H), 3.55 (d, J=4.6 Hz, 1H), 3.37 (s, 3H), 3.08 (s, 3H), 2.98 (s, 3H), 2.73 (m, 1H), 2.39 (s, 3H), 2.31 (d, J=8.7 Hz, 2H), 1.95 (s, 3H), 1.82-1.76 (m, 1H), 1.74 (s, 3H), 1.37 (s, 9H), 1.24 (s, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: A solution of 4 equiv 7a in dry CH2Cl2, was added with 1 equiv baccatin derivative, 2 equiv DCC, 0.5 equiv DMAP and 0.2 equiv PTSA, at room temperature with stirring overnight. The reaction was evaporated under reduced pressure. Chromatography of the crude mixture (n-hexane/EtOAc = 2:1) afforded 16 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: A solution of 4 equiv 7a in dry CH2Cl2, was added with 1 equiv baccatin derivative, 2 equiv DCC, 0.5 equiv DMAP and 0.2 equiv PTSA, at room temperature with stirring overnight. The reaction was evaporated under reduced pressure. Chromatography of the crude mixture (n-hexane/EtOAc = 2:1) afforded 16 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; | 10149] 7,10-Dimethoxyl-1,14-carbonate baccatin III (1 eq.) and (4S,5R)-3-t-butoxycarbonyl-2-(4-methoxyphenyl)- 4-phenyl-5-oxazolidine carboxylic acid (4 eq.) were dissolved in dichloromethane which was used as the solvent, into which 0.5 equivalents of DMAP and 2.0 equivalents of DCC were added successively to react overnight at room temperature. The obtained product was reacted in 2 equivalents of acetyl chloride/methanol solution to give the taxane derivative PCMI-01 as the final product. The overall yield of two steps was 71% and the purity of the final product was95% or higher. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: A solution of 4 equiv 7a in dry CH2Cl2, was added with 1 equiv baccatin derivative, 2 equiv DCC, 0.5 equiv DMAP and 0.2 equiv PTSA, at room temperature with stirring overnight. The reaction was evaporated under reduced pressure. Chromatography of the crude mixture (n-hexane/EtOAc = 2:1) afforded 16 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: A solution of 4 equiv 7a in dry CH2Cl2, was added with 1 equiv baccatin derivative, 2 equiv DCC, 0.5 equiv DMAP and 0.2 equiv PTSA, at room temperature with stirring overnight. The reaction was evaporated under reduced pressure. Chromatography of the crude mixture (n-hexane/EtOAc = 2:1) afforded 16 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: A solution of 4 equiv 7a in dry CH2Cl2, was added with 1 equiv baccatin derivative, 2 equiv DCC, 0.5 equiv DMAP and 0.2 equiv PTSA, at room temperature with stirring overnight. The reaction was evaporated under reduced pressure. Chromatography of the crude mixture (n-hexane/EtOAc = 2:1) afforded 16 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: A solution of 4 equiv 7a in dry CH2Cl2, was added with 1 equiv baccatin derivative, 2 equiv DCC, 0.5 equiv DMAP and 0.2 equiv PTSA, at room temperature with stirring overnight. The reaction was evaporated under reduced pressure. Chromatography of the crude mixture (n-hexane/EtOAc = 2:1) afforded 16 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: A solution of 4 equiv 7a in dry CH2Cl2, was added with 1 equiv baccatin derivative, 2 equiv DCC, 0.5 equiv DMAP and 0.2 equiv PTSA, at room temperature with stirring overnight. The reaction was evaporated under reduced pressure. Chromatography of the crude mixture (n-hexane/EtOAc = 2:1) afforded 16 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: A solution of 4 equiv 7a in dry CH2Cl2, was added with 1 equiv baccatin derivative, 2 equiv DCC, 0.5 equiv DMAP and 0.2 equiv PTSA, at room temperature with stirring overnight. The reaction was evaporated under reduced pressure. Chromatography of the crude mixture (n-hexane/EtOAc = 2:1) afforded 16 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: A solution of 4 equiv 7a in dry CH2Cl2, was added with 1 equiv baccatin derivative, 2 equiv DCC, 0.5 equiv DMAP and 0.2 equiv PTSA, at room temperature with stirring overnight. The reaction was evaporated under reduced pressure. Chromatography of the crude mixture (n-hexane/EtOAc = 2:1) afforded 16 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: A solution of 4 equiv 7a in dry CH2Cl2, was added with 1 equiv baccatin derivative, 2 equiv DCC, 0.5 equiv DMAP and 0.2 equiv PTSA, at room temperature with stirring overnight. The reaction was evaporated under reduced pressure. Chromatography of the crude mixture (n-hexane/EtOAc = 2:1) afforded 16 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: A solution of 4 equiv 7a in dry CH2Cl2, was added with 1 equiv baccatin derivative, 2 equiv DCC, 0.5 equiv DMAP and 0.2 equiv PTSA, at room temperature with stirring overnight. The reaction was evaporated under reduced pressure. Chromatography of the crude mixture (n-hexane/EtOAc = 2:1) afforded 16 as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; at 20℃; for 24h; | General procedure: Commercial (4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid (7, paclitaxel side chain,2 g, 0.005 mol, 1.00 equiv) and HATU (3 g, 0.0079 mol, 1.50equiv)were added to a solution of compound 6 (1 g, 0.0052 mol,1.00 equiv) in THF (50 mL), and the reaction mixturewas stirredat room temperature for 24 h. Then 150 mL water and CH2Cl2was added. The organic layer was washed with brine, driedover MgSO4, and evaporated to give a residue which waschromatographed over silica gel (Petroleumether:EtOAc = 1:3)to afford compound 9 as a white amorphous powder (2.252 g,86%) as a pair of diastereoisomers. Compound 10 was prepared through the coupling ofcompounds 6 and commercial (4S,5R)-3-tert-butoxycarbony-2-(4-methoxpheny)-4-phenyl-5-oxazolidinecarboxylic acid(8, docetaxel side chain) in 95% yields by similar procedures.Compound 10 is also a pair of diastereoisomers |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With dmap; dicyclohexyl-carbodiimide; In toluene; at 85℃; | General procedure: We synthesize compound 4-8 starting from 10-deacetylbaccatinIII(9), and 13 was obtained in three-step sequence: (1) the protection of 7,10-OH with TrocCl. The protection of 7,10-OH of 9 was achieved by treatment with TrocCl to give 10 in 81% yield; (2) Fischer-Speier Esterification. Esterification at C-13 of 10 was then realized with the 2-(4-OMe)phenyl-1,3-oxazolidine derivativeof N -Boc-phenylisoserine 11, DCC and DMAP in toluene at 85 leading tocompound 12 in good yield (92 %); (3)Selective deprotection of the Troc2,2,2-trichloroethyloxycarbonyl ether was accomplished using Zn/AcOH/MeOH. Weafford compounds 13 in good yield (90%). |
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; | 11mmol benzooxazoline carboxylic acid 8, 10mmol 7, 10-diTroc-acetylbaccatin 2, 20mmol DCC and 1mmol DMAP dissolve in CH2Cl2, under room temperature complete the reaction. Filter out the insoluble matter, the filtrate has been removed under reduced pressure and then obtained coupling product 9. | |
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 6℃; for 0.833333h;Inert atmosphere; | Under the protection of nitrogen, 8290.0 ml of dichloromethane and 99.5 g of 4-dimethylaminopyridine were added to the reactor, followed by 829.0 g of intermediate I and 746.1 g of (2S,4S,5R)-2-(4-methoxy Phenyl)-4-phenyl-3,5-oxazolidinedicarboxylic acid 3-tert-butyl ester was dissolved, 663.2g N,N-dicyclohexylcarbodiimide was added dropwise within 50min, and the drop temperature was 0 After the completion of the dropwise addition, the reaction temperature was controlled at 6C until the intermediate I raw material remained less than 0.5% to stop the reaction. After adding water to the reaction solution for quenching, the reaction solution was neutralized with 149.9 ml of dilute hydrochloric acid until the pH value was 6.0. The filtrate was collected by filtration and then concentrated. The obtained concentrate was recrystallized with an acetone-n-hexane system (the volume ratio of acetone and n-hexane was acetone:n-hexane=10:15) to obtain intermediate II. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 2.0h; | General procedure: To the solution of 7 (4.4 g, 11 mmol), 2/9 (10 mmol) and DMAP (0.12 g, 1 mmol) in CH2Cl2 (80 mL) was added DCC (4.12 g, 20 mmol) and the solution was stirred for 2 h at room temperature. Then, DCU was filtered off and the solution was concentrated under vacuum to get the crude compound 3/10 respectively, which were used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 2.0h; | General procedure: To the solution of 7 (4.4 g, 11 mmol), 2/9 (10 mmol) and DMAP (0.12 g, 1 mmol) in CH2Cl2 (80 mL) was added DCC (4.12 g, 20 mmol) and the solution was stirred for 2 h at room temperature. Then, DCU was filtered off and the solution was concentrated under vacuum to get the crude compound 3/10 respectively, which were used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; dicyclohexyl-carbodiimide; In toluene; at 60℃; | 7,10-Di-O-[2-(Chloroacetyl)]-13-[(4S, 5R)-2(-p-methoxyphenyl)-3-tert- butoxycarbonyl-4-phenyl-l,3-oxazolidinyl -5-carbonyl]-10-deacetylbaccatin III (4) Compound 4 is obtained from 7, 10-di-O-(2-chloroacetyl)- 10-deacetylbaccatin III (2, 100 g, 0.143 mol), (4S,5R)-3-(tert-butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyloxaz- olidine-5-carboxylic acid (5, 71.53 g, 179 mmol), DCC (36.9 g, 179 mmol) and 4- dimethyl- aminopyridine (4.80 g, 31.54 mmol) in toluene (1.0 L) and stirred for 5-8 h at 60 C , followed by the separation of the resulting dicyclohexylurea by filtration. The resulting cake was washed with 200 ml of toluene, and the combined organic layer was sequentially washed with 3L ml of 3N hydrochloric acid and 3L of saturated sodium bicarbonate and dried over anhydrous Na2S04, filtered and the organic solvent was removed from the filtrate under a reduced pressure. The residue is added into 1.2 L n- heptane and then mixed for another 2 hours. The resulting fine solid is filtered and then washed with 100 ml of heptane to afford pure compound 4 (Yield: 146.6 g, 0.136 mol, 90%) which is used in the next step without any purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.3% | With dmap; dicyclohexyl-carbodiimide; In toluene; at 25℃;Inert atmosphere; | Under the protection of Nu2, compound 4 (10.0 (^, 14.881 ^ 0.1), compound 2 (7.728, 19.34111) 101)(4.29 g, 20.83 mMol), DMAP (1.27 g, 10.42 mMol) and 60 ml of toluene were added thereto, and the mixture was stirred at 25 CNight, TLC detection of raw materials disappeared, filtered, diluted with water, ethyl acetate extraction 3 times, combined organic phase, organic phase has water andSaturated brine was washed twice, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a white solidThe crude product was purified by Flash column to give 16.20 g of a white solid (eluent: RhoEpsilon / EpsilonAlpha = 3/1, V / V)The white solid was recrystallized from dichloromethane / n-hexane to give 14.15 g of compound 1 as a white solid in a yield of 90.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In toluene; at 60℃;Inert atmosphere; | the 7,10-O-dibenzyloxycarbonyl-10- deacetyl baccatin III (5.6 g, 6.8mmol) , EDCI (2.8 g, 14.6 mmol), 4-N, N-dimethylpyridine (2.5 g, 20.4 mmol) was dissolved in toluene (100 mL) and warmed to 60 C under nitrogen. Then slowly dropwise added a solution of (4S, 5R) -3-tert-butoxycarbonyl-2- (4-methoxyphenyl) -4-phenyl-5-oxazolidine carboxylic acid (4.1g, 10.2mmol) in toluene (20ml) and the reaction was monitored by HPLC. After completion of the reaction, the mixture was cooled to room temperature. The reaction solution was washed successively with saturated ammonium chloride (15 mL X2), saturated aqueous sodium bicarbonate solution (20 mL X2) and saturated brine (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to remove the solvent, The residue was crystallized from dichloromethane-petroleum ether to give the title compound as a white solid. (7.3g, yield 90%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; In toluene; at 20℃;Inert atmosphere; | Weigh intermediate I, add side chain, 4-dimethylaminopyridine, and add dry toluene to dissolve.The condensing agent was added dropwise under the protection of nitrogen at a temperature of 20 C. After completion of the dropwise addition, the reaction was continued at a reaction temperature of 20 C. to Intermediate I. The residual amount of the starting material was less than 0.2%. The reaction liquid was stopped, and a crystallization solvent was added to the reaction mixture. Crystallize for 2.5 hours, filter dry to give intermediate II.Among them, the side chain group compound is (4S,5R)-2-(4-methoxyphenyl)-4-phenyl-3,5-oxazolidinedicarboxylate.Acid-3-tert-butyl ester, crystallization solvent is petroleum ether, condensing agent is diisopropylcarbodiimide; intermediate I, side chain group compound, 4-dimethylaminopyridine, toluene, condensing agent, petroleum ether The mass to use ratio is 1:0.8:0.13:8:0.3:14. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With dmap; dicyclohexyl-carbodiimide; In toluene; at 15℃; for 2.0h; | (2) The product I (7.5 g) was dissolved in 75 ml of toluene, and 4-dimethylaminopyridine (0.7 g), doxyside acid (4.5 g) and N,N-Dicyclohexylcarbimide (3.3 g, 1.7 eq.) was reacted at 15 C for 2 h. The reaction mixture was suction filtered, and the filtrate was washed with dil. The concentrated liquid was added to n-heptane (150 ml) which was stirred, and a large amount of solid was precipitated, suction filtered, and dried to give the product II (10.3 g) in a yield of 93.0%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; | General procedure: Oridonin (100 mg, 0.27 mmol) wasmixed with 4-methoxycinnamic acid (48 mg, 0.27 mmol),EDCI(157 mg, 0.82 mmol) and DMAP(101 mg, 0.82 mmol) in drydichloromethane(10 mL) and stirred at room temperature overnight.The mixturewas poured into 1MHCl solution, and extractedwith dichloromethane. The organic layer was combined, washedwith water and saturated NaCl solutions, dried over anhydrousMgSO4, filtered, and concentrated in vacuo. The crude product waspurified by column chromatography to give the compound 20(122 mg, 86%) as a white solid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.1% | With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 1.0h; | (2) 7,10-(di)Troc-10-DAB 364.1gAdd to 3641 mL of dichloromethane to dissolve,A clear solution was added 145.6g of docetaxel side chain after(4S, 5R) -3- (N- tert-butoxycarbonyl) -2-p-methoxyphenyl-4-phenyl-1,3-oxazolidin-5-carboxylic acid,Then add catalyst 7.3g DMAPAnd 163.8g DCC,Reaction at room temperature for 1 h,After the reaction is over, quickly filter and add water to inactivate,Extracted once with a volume concentration of 5% aqueous hydrochloric acid and saturated sodium bicarbonate solution.The organic phase was collected at 40 sucked dry under reduced pressure to give intermediate 491.73g,93%, the yield is 97.1%; |
Tags: 196404-55-4 synthesis path| 196404-55-4 SDS| 196404-55-4 COA| 196404-55-4 purity| 196404-55-4 application| 196404-55-4 NMR| 196404-55-4 COA| 196404-55-4 structure
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Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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