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(R)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide
ramatroban
Conditions | Yield |
---|---|
Stage #1: (R)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide With water; sodium hydroxide In isopropyl alcohol at 100℃; for 24h; Stage #2: With hydrogenchloride In water | 79% |
acrylonitrile
(R)-4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide
ramatroban
Conditions | Yield |
---|---|
With potassium hydroxide; sodium hydride 1.) dimethylformamide, 2 h, room temperature, 2.) isopropanol, reflux, 16 h; Yield given. Multistep reaction; |
1,2,3,4-tetrahydrocarbazol-3-one
ramatroban
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 2.) tetrabutylammonium borohydride, 3.) 2N sulfuric acid / 1.) benzene, reflux, 1 h, 2.) CH2Cl2, -50 deg C to room temperature, 3.) methanol, room temperature, 1 h 2: 1.) 2N NaOH, conc. HCl, 2.) ammonium formiate / 2.) 10percent Pd/C / 1.) methanol, ethyl acetate, 2.) dimethylformamide, reflux, 20 min 3: 84 percent / triethylamine / CH2Cl2 / 1 h / Ambient temperature 4: 1.) 80percent sodium hydride (in mineral oil), 2.) 10percent potassium hydroxide / 1.) dimethylformamide, 2 h, room temperature, 2.) isopropanol, reflux, 16 h View Scheme | |
Multi-step reaction with 6 steps 1.1: D-glucose / water / 24 h / 30 °C / Enzymatic reaction 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 2.2: 10 h / -25 - -15 °C 3.1: water; triphenylphosphine / 15 h / 65 °C 4.1: triethylamine / dichloromethane / 1 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 5.2: 1 h / 20 °C 6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere 2.1: Candida antarctica Lipase A / tetrahydrofuran / 5 h / 30 °C / Enzymatic reaction 3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 3.2: 10 h / -25 - -15 °C 4.1: water; triphenylphosphine / 15 h / 65 °C 5.1: triethylamine / dichloromethane / 1 h / 20 °C 6.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 6.2: 1 h / 20 °C 7.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme |
ramatroban
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) 2N NaOH, conc. HCl, 2.) ammonium formiate / 2.) 10percent Pd/C / 1.) methanol, ethyl acetate, 2.) dimethylformamide, reflux, 20 min 2: 84 percent / triethylamine / CH2Cl2 / 1 h / Ambient temperature 3: 1.) 80percent sodium hydride (in mineral oil), 2.) 10percent potassium hydroxide / 1.) dimethylformamide, 2 h, room temperature, 2.) isopropanol, reflux, 16 h View Scheme |
(3R)-2,3,4,9-tetrahydro-1H-carbazol-3-amine
ramatroban
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 84 percent / triethylamine / CH2Cl2 / 1 h / Ambient temperature 2: 1.) 80percent sodium hydride (in mineral oil), 2.) 10percent potassium hydroxide / 1.) dimethylformamide, 2 h, room temperature, 2.) isopropanol, reflux, 16 h View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 1 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 2.2: 1 h / 20 °C 3.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme |
cyclohexanedione monoethylene ketal
ramatroban
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C 1.2: 4 h / 110 °C 2.1: trifluoroacetic acid / acetone / 24 h / 65 °C 3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere 4.1: Candida antarctica Lipase A / tetrahydrofuran / 5 h / 30 °C / Enzymatic reaction 5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 6.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C 7.1: water; triphenylphosphine / 15 h / 65 °C 8.1: triethylamine / dichloromethane / 1 h / 20 °C 9.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 9.2: 1 h / 20 °C 10.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C 1.2: 4 h / 110 °C 2.1: trifluoroacetic acid / acetone / 24 h / 65 °C 3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere 4.1: Pseudomonas cepacia lipase / tetrahydrofuran / 8 h / 30 °C / Enzymatic reaction 5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 6.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C 7.1: water; triphenylphosphine / 15 h / 65 °C 8.1: triethylamine / dichloromethane / 1 h / 20 °C 9.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 9.2: 1 h / 20 °C 10.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C 1.2: 4 h / 110 °C 2.1: trifluoroacetic acid / acetone / 24 h / 65 °C 3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere 4.1: Candida antarctica lipase B / tetrahydrofuran / 8 h / 30 °C / Enzymatic reaction 5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 6.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C 7.1: water; triphenylphosphine / 15 h / 65 °C 8.1: triethylamine / dichloromethane / 1 h / 20 °C 9.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 9.2: 1 h / 20 °C 10.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme |
(S)-2,3,4,9-tetrahydro-1H-carbazol-3-yl methanesulfonate
ramatroban
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium azide / dimethyl sulfoxide / 24 h / 20 °C 2.1: water; triphenylphosphine / 15 h / 65 °C 3.1: triethylamine / dichloromethane / 1 h / 20 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 4.2: 1 h / 20 °C 5.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C 2.1: water; triphenylphosphine / 15 h / 65 °C 3.1: triethylamine / dichloromethane / 1 h / 20 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 4.2: 1 h / 20 °C 5.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme |
(R)-3-azido-2,3,4,9-tetrahydro-1H-carbazole
ramatroban
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: water; triphenylphosphine / 15 h / 65 °C 2.1: triethylamine / dichloromethane / 1 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 3.2: 1 h / 20 °C 4.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme |
4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide
ramatroban
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 20 °C 1.2: 20 °C 2.1: chiralpak IC / hexane; isopropyl alcohol / 40 °C / Resolution of racemate 3.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: chiralpak IC / hexane; isopropyl alcohol / 30 °C / Resolution of racemate 2.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 2.2: 1 h / 20 °C 3.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme |
ramatroban
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: chiralpak IC / hexane; isopropyl alcohol / 40 °C / Resolution of racemate 2: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme |
ramatroban
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: sodium azide / 24 h 2.1: chiralcel OD / hexane; isopropyl alcohol / 30 °C / Resolution of racemate 3.1: water; triphenylphosphine / 15 h / 65 °C 4.1: triethylamine / dichloromethane / 1 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 5.2: 1 h / 20 °C 6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: sodium azide / 24 h 2.1: palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C 3.1: triethylamine / dichloromethane / 20 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 20 °C 4.2: 20 °C 5.1: chiralpak IC / hexane; isopropyl alcohol / 40 °C / Resolution of racemate 6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: sodium azide / 24 h 2.1: palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C 3.1: triethylamine / dichloromethane / 20 °C 4.1: chiralpak IC / hexane; isopropyl alcohol / 30 °C / Resolution of racemate 5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 5.2: 1 h / 20 °C 6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: chiralcel OD / hexane; isopropyl alcohol / 40 °C / Resolution of racemate 2.1: sodium azide / dimethyl sulfoxide / 24 h / 20 °C 3.1: water; triphenylphosphine / 15 h / 65 °C 4.1: triethylamine / dichloromethane / 1 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 5.2: 1 h / 20 °C 6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: chiralcel OD / hexane; isopropyl alcohol / 40 °C / Resolution of racemate 2.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C 3.1: water; triphenylphosphine / 15 h / 65 °C 4.1: triethylamine / dichloromethane / 1 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 5.2: 1 h / 20 °C 6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme |
(S)-(-)-2,3,4,9-tetrahydro-1H-carbazol-3-ol
ramatroban
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 1.2: 10 h / -25 - -15 °C 2.1: water; triphenylphosphine / 15 h / 65 °C 3.1: triethylamine / dichloromethane / 1 h / 20 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 4.2: 1 h / 20 °C 5.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C 3.1: water; triphenylphosphine / 15 h / 65 °C 4.1: triethylamine / dichloromethane / 1 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 5.2: 1 h / 20 °C 6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2.1: sodium azide / dimethyl sulfoxide / 24 h / 20 °C 3.1: water; triphenylphosphine / 15 h / 65 °C 4.1: triethylamine / dichloromethane / 1 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 5.2: 1 h / 20 °C 6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme |
(+/-)-2,3,4,9-tetrahydro-1H-carbazol-3-ol
ramatroban
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: Candida antarctica Lipase A / tetrahydrofuran / 5 h / 30 °C / Enzymatic reaction 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 2.2: 10 h / -25 - -15 °C 3.1: water; triphenylphosphine / 15 h / 65 °C 4.1: triethylamine / dichloromethane / 1 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 5.2: 1 h / 20 °C 6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: Candida antarctica lipase B / tetrahydrofuran / 8 h / 30 °C / Enzymatic reaction 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 2.2: 10 h / -25 - -15 °C 3.1: water; triphenylphosphine / 15 h / 65 °C 4.1: triethylamine / dichloromethane / 1 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 5.2: 1 h / 20 °C 6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: Pseudomonas cepacia lipase / tetrahydrofuran / 8 h / 30 °C / Enzymatic reaction 2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 2.2: 10 h / -25 - -15 °C 3.1: water; triphenylphosphine / 15 h / 65 °C 4.1: triethylamine / dichloromethane / 1 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 5.2: 1 h / 20 °C 6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme |
4-Fluorobenzenesulfonyl chloride
ramatroban
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 1 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 2.2: 1 h / 20 °C 3.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme |
ramatroban
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C 2.1: triethylamine / dichloromethane / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 20 °C 3.2: 20 °C 4.1: chiralpak IC / hexane; isopropyl alcohol / 40 °C / Resolution of racemate 5.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C 2.1: triethylamine / dichloromethane / 20 °C 3.1: chiralpak IC / hexane; isopropyl alcohol / 30 °C / Resolution of racemate 4.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 4.2: 1 h / 20 °C 5.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: chiralcel OD / hexane; isopropyl alcohol / 30 °C / Resolution of racemate 2.1: water; triphenylphosphine / 15 h / 65 °C 3.1: triethylamine / dichloromethane / 1 h / 20 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 4.2: 1 h / 20 °C 5.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme |
2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine
ramatroban
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 20 °C 2.2: 20 °C 3.1: chiralpak IC / hexane; isopropyl alcohol / 40 °C / Resolution of racemate 4.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 20 °C 2.1: chiralpak IC / hexane; isopropyl alcohol / 30 °C / Resolution of racemate 3.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 3.2: 1 h / 20 °C 4.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme |
phenylhydrazine
ramatroban
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C 1.2: 4 h / 110 °C 2.1: trifluoroacetic acid / acetone / 24 h / 65 °C 3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere 4.1: Candida antarctica Lipase A / tetrahydrofuran / 5 h / 30 °C / Enzymatic reaction 5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 6.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C 7.1: water; triphenylphosphine / 15 h / 65 °C 8.1: triethylamine / dichloromethane / 1 h / 20 °C 9.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 9.2: 1 h / 20 °C 10.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C 1.2: 4 h / 110 °C 2.1: trifluoroacetic acid / acetone / 24 h / 65 °C 3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere 4.1: Pseudomonas cepacia lipase / tetrahydrofuran / 8 h / 30 °C / Enzymatic reaction 5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 6.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C 7.1: water; triphenylphosphine / 15 h / 65 °C 8.1: triethylamine / dichloromethane / 1 h / 20 °C 9.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 9.2: 1 h / 20 °C 10.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C 1.2: 4 h / 110 °C 2.1: trifluoroacetic acid / acetone / 24 h / 65 °C 3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere 4.1: Candida antarctica lipase B / tetrahydrofuran / 8 h / 30 °C / Enzymatic reaction 5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 6.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C 7.1: water; triphenylphosphine / 15 h / 65 °C 8.1: triethylamine / dichloromethane / 1 h / 20 °C 9.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 9.2: 1 h / 20 °C 10.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme |
(R)-4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide
ramatroban
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 1.2: 1 h / 20 °C 2.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme |
1,2,4,9-tetrahydrospiro[3H-carbazole-3,2*-[1,3]doxolane]
ramatroban
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: trifluoroacetic acid / acetone / 24 h / 65 °C 2.1: D-glucose / water / 24 h / 30 °C / Enzymatic reaction 3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 3.2: 10 h / -25 - -15 °C 4.1: water; triphenylphosphine / 15 h / 65 °C 5.1: triethylamine / dichloromethane / 1 h / 20 °C 6.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 6.2: 1 h / 20 °C 7.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: trifluoroacetic acid / acetone / 24 h / 65 °C 2.1: D-glucose / water / 24 h / 30 °C / Enzymatic reaction 3.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 4.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C 5.1: water; triphenylphosphine / 15 h / 65 °C 6.1: triethylamine / dichloromethane / 1 h / 20 °C 7.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 7.2: 1 h / 20 °C 8.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: trifluoroacetic acid / acetone / 24 h / 65 °C 2.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere 3.1: Candida antarctica Lipase A / tetrahydrofuran / 5 h / 30 °C / Enzymatic reaction 4.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 4.2: 10 h / -25 - -15 °C 5.1: water; triphenylphosphine / 15 h / 65 °C 6.1: triethylamine / dichloromethane / 1 h / 20 °C 7.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C 7.2: 1 h / 20 °C 8.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C View Scheme |
methanol
ramatroban
(R)-methyl 3-[3-(4-fluorophenylsulfonamido)-3,4-dihydro-1H-carbazol-9(2H)-yl]propanoate
Conditions | Yield |
---|---|
With sulfuric acid In water at 65℃; for 15h; | 60% |
ramatroban
Conditions | Yield |
---|---|
With sodium hydroxide |
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