N,O-双三甲硅基乙酰胺

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

实验步骤: 2.28 g of 7-amino-3-formyl-3-cephem-4-carboxylic acid are bisilylated as described in example 19 with 5.4 ml of N,O-bis-(trimethylsilyl)-acetamide, reacted with phenylacetic acid chloride, and then hydrolysed with 0.4 ml of water. The hydrolysed reaction mixture is treated with 1 g of activated charcoal and then filtered. The yellow filtrate is mixed with 20 ml of a 10% solution of diphenyldiazomethane in dichloromethane, and then concentrated to 10 ml in vacuo. The product is precipitated from the residue of evaporation thus obtained by adding 100 ml of n-hexane. 7-phenylacetamido-3-formyl-3-cephem-4-carboxylic acid benzhydrylester is thus obtained as a slightly yellowish product. filtered The yellow filtrate is mixed with 20 ml of a 10% solution of diphenyldiazomethane in dichloromethane concentrated to 10 ml in vacuo The product is precipitated from the residue of evaporation thus obtained

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

实验步骤: 2.28 g of 7-amino-3-formyl-3-cephem-4-carboxylic acid are bisilylated as described in example 19 with 5.4 ml of N,O-bis-(trimethylsilyl)-acetamide, reacted with phenylacetic acid chloride, and then hydrolysed with 0.4 ml of water. The hydrolysed reaction mixture is treated with 1 g of activated charcoal and then filtered. The yellow filtrate is mixed with 20 ml of a 10% solution of diphenyldiazomethane in dichloromethane, and then concentrated to 10 ml in vacuo. The product is precipitated from the residue of evaporation thus obtained by adding 100 ml of n-hexane. 7-phenylactamido-3-formyl-3-cephem-4-carboxylic acid benzhydrylester is thus obtained as a slightly yellowish product. 1H-NMR (60 MHz, d6 -DMSO): 3.15 (ABq, J=18 Hz, 2H, SCH2); 3.55 (s, 2H, --CH2 --CO); 4.9 (d, J=5 Hz, 1H, H-6); 5.90 (dd, J=5 and 8 Hz, 1H, H-7); 6.6 (d, J=8 Hz, 1H, NH); 7.0 (s, 1H, CHPh2); 7.25 and 7.30 (2s, 15H, Ar--H); 9.62 (s, 1H, CH=O). filtered The yellow filtrate is mixed with 20 ml of a 10% solution of diphenyldiazomethane in dichloromethane concentrated to 10 ml in vacuo The product is precipitated from the residue of evaporation thus obtained

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

实验步骤: 2 gms of 5-Benzyloxy-2-[(4-benzyloxy-phenyl)-(4-fluoro-phenylamino)-methyl]-5-(4-fluoro-phenyl)-pentanoic acid methyl ester was dissolved in 20 ml of toluene and stirred at room temperature for 5-20 minutes. To the reaction mass 2.39 ml of N,O-Bis-(trimethylsilyl)-acetamide was added and temperature was raised to 40-60° C. To this 0.04 gms of Tetra butyl ammonium fluoride was added and reaction was monitored by TLC. Water was added and organic fraction was distilled to get 1.5 gms of 3-[3-Benzyloxy-3-(4-fluoro-phenyl)-propyl]-4-(4-benzyloxy-phenyl)-1-(4-fluoro-phenyl)-azetidin-2-one. temperature was raised to 40-60° C reaction organic fraction was distilled

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

实验步骤: To a mixture of 2-amino-4-methyl-thiazole-carboxylic acid (2-hydroxyethyl)-amide (0.2 g) in dichloromethane was added N,O-bis-(trimethylsilyl)-acetamide (0.2 g) and the mixture stirred for 12 h. CDI (0.16 g) and DMAP (6 mg) was then added and the mixture stirred for 12 h before addition of dicyclohexylamine (0.18 g). After stirring overnight waster was added and the aqueous phase extracted with dichloromethane, concentrated and purified by chromatography to give the title compound. After stirring overnight waster was added the aqueous phase extracted with dichloromethane concentrated purified by chromatography

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

实验步骤: 2.28 g of 7-amino-3-formyl-3-cephem-4-carboxylic acid are bisilylated as described in example 19 with 5.4 ml of N,O-bis-(trimethylsilyl)-acetamide, reacted with phenylacetic acid chloride, and then hydrolysed with 0.4 ml of water. The hydrolysed reaction mixture is treated with 1 g of activated charcoal and then filtered. The yellow filtrate is mixed with 20 ml of a 10% solution of diphenyldiazomethane in dichloromethane, and then concentrated to 10 ml in vacuo. The product is precipitated from the residue of evaporation thus obtained by adding 100 ml of n-hexane. 7-phenylacetamido-3-formyl-3-cephem-4-carboxylic acid benzhydrylester is thus obtained as a slightly yellowish product. filtered The yellow filtrate is mixed with 20 ml of a 10% solution of diphenyldiazomethane in dichloromethane concentrated to 10 ml in vacuo The product is precipitated from the residue of evaporation thus obtained

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 1-cyclopentyl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one (3.40 g) in DMF (42.0 mL) was added trimethylsilyl N-(trimethylsilyl)ethanimidate (7.52 g) at room temperature, and the mixture was stirred at 40° C. for 3 hr. The reaction mixture was allowed to be cooled to room temperature, and NBS (3.59 g) was added thereto at room temperature. The reaction mixture was stirred overnight at room temperature, water was added thereto, and the mixture was stirred at room temperature for 2 hr. The white precipitate was collected by filtration, and dried under reduced pressure to give the title compound (3.28 g). to be cooled to room temperature at room temperature The reaction mixture was stirred overnight at room temperature the mixture was stirred at room temperature for 2 hr The white precipitate was collected by filtration dried under reduced pressure

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 1-cyclopentyl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one (3.40 g) in DMF (42.0 mL) was added trimethylsilyl N-(trimethylsilyl)ethanimidate (7.52 g) at room temperature, and the mixture was stirred at 40° C. for 3 hr. The reaction mixture was allowed to be cooled to room temperature, and NBS (3.59 g) was added thereto at room temperature. The reaction mixture was stirred overnight at room temperature, water was added thereto, and the mixture was stirred at room temperature for 2 hr. The white precipitate was collected by filtration, and dried under reduced pressure to give the title compound (3.28 g). to be cooled to room temperature at room temperature The reaction mixture was stirred overnight at room temperature the mixture was stirred at room temperature for 2 hr The white precipitate was collected by filtration dried under reduced pressure

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 1-cyclopentyl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one (3.40 g) in DMF (42.0 mL) was added trimethylsilyl N-(trimethylsilyl)ethanimidate (7.52 g) at room temperature, and the mixture was stirred at 40° C. for 3 hr. The reaction mixture was allowed to be cooled to room temperature, and NBS (3.59 g) was added thereto at room temperature. The reaction mixture was stirred overnight at room temperature, water was added thereto, and the mixture was stirred at room temperature for 2 hr. The white precipitate was collected by filtration, and dried under reduced pressure to give the title compound (3.28 g). to be cooled to room temperature at room temperature The reaction mixture was stirred overnight at room temperature the mixture was stirred at room temperature for 2 hr The white precipitate was collected by filtration dried under reduced pressure

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

实验步骤: 2.28 g of 7-amino-3-formyl-3-cephem-4-carboxylic acid are bisilylated as described in example 19 with 5.4 ml of N,O-bis-(trimethylsilyl)-acetamide, reacted with phenylacetic acid chloride, and then hydrolysed with 0.4 ml of water. The hydrolysed reaction mixture is treated with 1 g of activated charcoal and then filtered. The yellow filtrate is mixed with 20 ml of a 10% solution of diphenyldiazomethane in dichloromethane, and then concentrated to 10 ml in vacuo. The product is precipitated from the residue of evaporation thus obtained by adding 100 ml of n-hexane. 7-phenylacetamido-3-formyl-3-cephem-4-carboxylic acid benzhydrylester is thus obtained as a slightly yellowish product. filtered The yellow filtrate is mixed with 20 ml of a 10% solution of diphenyldiazomethane in dichloromethane concentrated to 10 ml in vacuo The product is precipitated from the residue of evaporation thus obtained

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

实验步骤: 2.28 g of 7-amino-3-formyl-3-cephem-4-carboxylic acid are bisilylated as described in example 19 with 5.4 ml of N,O-bis-(trimethylsilyl)-acetamide, reacted with phenylacetic acid chloride, and then hydrolysed with 0.4 ml of water. The hydrolysed reaction mixture is treated with 1 g of activated charcoal and then filtered. The yellow filtrate is mixed with 20 ml of a 10% solution of diphenyldiazomethane in dichloromethane, and then concentrated to 10 ml in vacuo. The product is precipitated from the residue of evaporation thus obtained by adding 100 ml of n-hexane. 7-phenylactamido-3-formyl-3-cephem-4-carboxylic acid benzhydrylester is thus obtained as a slightly yellowish product. 1H-NMR (60 MHz, d6 -DMSO): 3.15 (ABq, J=18 Hz, 2H, SCH2); 3.55 (s, 2H, --CH2 --CO); 4.9 (d, J=5 Hz, 1H, H-6); 5.90 (dd, J=5 and 8 Hz, 1H, H-7); 6.6 (d, J=8 Hz, 1H, NH); 7.0 (s, 1H, CHPh2); 7.25 and 7.30 (2s, 15H, Ar--H); 9.62 (s, 1H, CH=O). filtered The yellow filtrate is mixed with 20 ml of a 10% solution of diphenyldiazomethane in dichloromethane concentrated to 10 ml in vacuo The product is precipitated from the residue of evaporation thus obtained

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

实验步骤: 2 gms of 5-Benzyloxy-2-[(4-benzyloxy-phenyl)-(4-fluoro-phenylamino)-methyl]-5-(4-fluoro-phenyl)-pentanoic acid methyl ester was dissolved in 20 ml of toluene and stirred at room temperature for 5-20 minutes. To the reaction mass 2.39 ml of N,O-Bis-(trimethylsilyl)-acetamide was added and temperature was raised to 40-60° C. To this 0.04 gms of Tetra butyl ammonium fluoride was added and reaction was monitored by TLC. Water was added and organic fraction was distilled to get 1.5 gms of 3-[3-Benzyloxy-3-(4-fluoro-phenyl)-propyl]-4-(4-benzyloxy-phenyl)-1-(4-fluoro-phenyl)-azetidin-2-one. temperature was raised to 40-60° C reaction organic fraction was distilled

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

实验步骤: To a mixture of 2-amino-4-methyl-thiazole-carboxylic acid (2-hydroxyethyl)-amide (0.2 g) in dichloromethane was added N,O-bis-(trimethylsilyl)-acetamide (0.2 g) and the mixture stirred for 12 h. CDI (0.16 g) and DMAP (6 mg) was then added and the mixture stirred for 12 h before addition of dicyclohexylamine (0.18 g). After stirring overnight waster was added and the aqueous phase extracted with dichloromethane, concentrated and purified by chromatography to give the title compound. After stirring overnight waster was added the aqueous phase extracted with dichloromethane concentrated purified by chromatography