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Chloromethyl pivalate
methicillin sodium
methicillin t. butylcarbonyloxymethyl ester
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 6h; Ambient temperature; | 56% |
methicillin sodium
(4S)-2t-[(2,6-dimethoxy-benzoylamino)-methyl]-5,5-dimethyl-thiazolidine-4r-carboxylic acid
Conditions | Yield |
---|---|
(i) aq. NaOH, (ii) aq. EtOH; Multistep reaction; |
methicillin sodium
(6aR)-6t,12t-bis-(2,6-dimethoxy-benzoylamino)-2,2,8,8-tetramethyl-5,11-dioxo-(6ar,12ac)-octahydro-bisthiazolo[3,2-a;3',2'-e][1,5]diazocine-3c,9c-dicarboxylic acid
Conditions | Yield |
---|---|
With hydrogen cation; 4-methyl-2-pentanone for 168h; Ambient temperature; |
methicillin sodium
N-[2-(2,6-dimethoxy-phenyl)-5-oxo-oxazol-4-ylidenemethyl]-D-penicillamine
Conditions | Yield |
---|---|
(i) aq. HgCl2, (ii) aq. H2S; Multistep reaction; |
chlorosulfuric acid chloromethyl ester
methicillin sodium
chloromethyl <2S-(2α,5α,6β)>-3,3-dimethyl-7-oxo-6-(2,6-dimethoxybenzamido)-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water for 0.5h; below 30 deg C; | 4.24 g |
With sodium hydrogencarbonate; tetra(n-butyl)ammonium hydrogen sulfate In dichloromethane; water |
methicillin sodium
<(3-pyridinylcarbonyl)oxy>methyl <2S-(2α,5α,6β)>-3,3-dimethyl-7-oxo-6-(2,6-dimethoxybenzamido)-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 4.24 g / NaHCO3, tetrabutylammonium hydrogen sulfate / H2O; CH2Cl2 / 0.5 h / below 30 deg C 2: 3 g / dimethylformamide / 144 h / Ambient temperature View Scheme |
methicillin sodium
<<(1,4-dihydro-1-methyl-3-pyridinyl)carbonyl>oxy>methyl <2S-(2α,5α,6β)>-3,3-dimethyl-7-oxo-6-(2,6-dimethoxybenzamido)-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 4.24 g / NaHCO3, tetrabutylammonium hydrogen sulfate / H2O; CH2Cl2 / 0.5 h / below 30 deg C 2: 3 g / dimethylformamide / 144 h / Ambient temperature 3: 1.6 g / nitromethane / 168 h / 20 - 25 °C 4: 0.25 g / Na2S2O4, NaHCO3 / ethyl acetate; H2O / 1.17 h / 0 - 5 °C View Scheme |
methicillin sodium
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 4.24 g / NaHCO3, tetrabutylammonium hydrogen sulfate / H2O; CH2Cl2 / 0.5 h / below 30 deg C 2: 3 g / dimethylformamide / 144 h / Ambient temperature 3: 1.6 g / nitromethane / 168 h / 20 - 25 °C View Scheme |
methicillin sodium
(2R,4S)-2-[(R)-(2,6-Dimethoxy-benzoylamino)-hydroxycarbamoyl-methyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 56 percent / dimethylformamide / 6 h / Ambient temperature 2: 100 percent / hydroxylaminehydrochloride, NaOH / methanol / 1.) -30 deg C to 20 deg C for 1h, 2.) room temperature, 1h View Scheme |
methicillin sodium
(6aR)-6t,12t-bis-(2,6-dimethoxy-benzoylamino)-2,2,8,8-tetramethyl-5,11-dioxo-(6ar,12ac)-octahydro-bisthiazolo[3,2-a;3',2'-e][1,5]diazocine-3c,9c-dicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: MeCOiBu, H+ / 168 h / Ambient temperature 2: diethyl ether; methanol View Scheme |
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