(4S,5R)-2-dichloromethyl-4-fluoromethyl-4,5-dihydro-5-(4-(methylsulfonyl)phenyl)oxazoline
Florfenicol
Conditions | Yield |
---|---|
With hydrogenchloride In water; isopropyl alcohol at 70℃; for 5h; pH=6; | 99% |
With potassium acetate In methanol; water; isopropyl alcohol for 3h; Heating; pH 5; Yield given; | |
With ammonium hydroxide; water at 25℃; | |
With sodium acetate In water; isopropyl alcohol for 3h; pH=5; Reflux; | 4.15 g |
In water; isopropyl alcohol at 80℃; for 1h; | 9.2 g |
dichloroacetic acid methyl ester
(1R,2S)-2-amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol
Florfenicol
Conditions | Yield |
---|---|
With triethylamine In methanol at 20℃; | 96% |
With triethylamine In methanol for 18h; Ambient temperature; | 84% |
With triethylamine for 3.5h; Heating; Yield given; |
(1R,2S)-1-(4-methylsulfonylphenyl)-2-benzylamino-3-fluoro-1-propanol
ethyl 1,1-dichloroacetate
Florfenicol
Conditions | Yield |
---|---|
Stage #1: (1R,2S)-1-(4-methylsulfonylphenyl)-2-benzylamino-3-fluoro-1-propanol With sulfuric acid; hydrogen; palladium on activated charcoal In ethanol at 20℃; for 2h; Stage #2: ethyl 1,1-dichloroacetate With triethylamine In methanol at 30℃; for 6h; Further stages.; | 96% |
dichloroacetic acid methyl ester
Florfenicol
Conditions | Yield |
---|---|
With triethylamine In methanol Heating; | 95% |
With sodium hydrogencarbonate In methanol at 50℃; for 16h; | 5.6 g |
With triethylamine In methanol at 50℃; for 10h; | 7.1 g |
Florfenicol
Conditions | Yield |
---|---|
With methanol; sodium acetate at 60℃; for 1h; Reagent/catalyst; | 95% |
D-threo-2-(dichloromethyl)-5-(4-methanesulfonylphenyl)-4,5-dihydro-1,3-oxazol-4-yl methanol
Florfenicol
Conditions | Yield |
---|---|
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In dichloromethane at 15 - 25℃; under 1520.1 - 2280.15 Torr; for 24h; | 93% |
Multi-step reaction with 2 steps 1: CF3CHCF2NEt2 / CH2Cl2 / 2 h / 100 °C 2: KOAc / methanol; propan-2-ol; H2O / 3 h / Heating; pH 5 View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 25 °C 2: triethylamine tris(hydrogen fluoride) / acetonitrile / 10 h / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: phosgene / dichloromethane / 16 h / 20 - 25 °C / Cooling with ice 2: sodium fluoride / N,N-dimethyl-formamide / 7 h / 80 °C / Inert atmosphere 3: hydrogenchloride / isopropyl alcohol; water / 5 h / 70 °C / pH 6 View Scheme |
dichloroacetic acid methyl ester
Florfenicol
Conditions | Yield |
---|---|
Stage #1: (1R,2S)-3-fluoro-1-(4-(methylsulfonyl)phenyl)-2-nitropropan-1-ol With palladium 10% on activated carbon; hydrogen In methanol Stage #2: dichloroacetic acid methyl ester With triethylamine In methanol at 20℃; for 18h; | 70% |
C13H15Cl2NO6S2
Florfenicol
Conditions | Yield |
---|---|
With triethylamine tris(hydrogen fluoride) In acetonitrile for 10h; Reflux; | 65% |
dichloroacetic acid methyl ester
(4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone
Florfenicol
Conditions | Yield |
---|---|
Stage #1: (4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone With sodium hydroxide In ethanol at 80℃; for 3h; Stage #2: With sodium acetate In tetrahydrofuran at 0℃; for 0.166667h; Stage #3: dichloroacetic acid methyl ester In tetrahydrofuran at 25℃; for 5h; | 56% |
Florfenicol
Conditions | Yield |
---|---|
Stage #1: 2,2-dichloro-N-{(4R,5R)-4-[4-(methylsulfonyl)phenyl]-2,2-dioxido-1,3,2-dioxathian-5-yl}acetamide With triethylamine tris(hydrogen fluoride) In 1,2-dichloro-ethane at 70℃; for 8h; Stage #2: With hydrogenchloride In ethyl acetate at 0℃; for 2h; | 35% |
Conditions | Yield |
---|---|
With sodium hydroxide In water pH=4.54 - 5.53; Conversion of starting material; | A 0.17% B 0.93% |
With ethanolamine In water pH=4.48 - 5.51; Conversion of starting material; | A 0.18% B 0.7% |
dichloroacetic acid methyl ester
(1R,2S)-2-(2,3-dimethylbenzoyl)amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol
A
thiamphenicol
B
Florfenicol
Conditions | Yield |
---|---|
With hydrogenchloride; triethylamine 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given; |
(1R,2R)-2-(2,2-dichloro-acetylamino)-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol
Florfenicol
Conditions | Yield |
---|---|
Multistep reaction; |
dichloroacetic acid methyl ester
(1R,2S)-2-amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol
B
Florfenicol
Conditions | Yield |
---|---|
In methanol; water; toluene |
para-methanesulfonylbenzaldehyde
Florfenicol
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 83 percent / piperidine / pyridine / 4 h / 95 - 100 °C 2: 1.) SOCl2, 2.) NaBH4 / 1) reflux, 1 h; 2) CH2Cl2, EtOH, 10 deg C, 1 h 3: 82 percent / 4 Anstroem molecular sieves, diisopropyl L-tartrate, Ti(OPr-i)4, t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / 4 h / -20 °C 4: 1.) NaH, 2.) ZnCl2, 3.) 4 Angstroem molecular sieves / 1) THF, 5 deg C, 30 min; 2) THF, 5 deg C, 30 min; 3) THF, 55 deg C, 16 h 5: 1.) Et3N, MeSO2Cl, 2.) aq. NaOH / 1) pyridine, 5 deg C, 2 h; 2) pyridine, pH 12.5 6: CF3CHCF2NEt2 / CH2Cl2 / 2 h / 100 °C 7: KOAc / methanol; propan-2-ol; H2O / 3 h / Heating; pH 5 View Scheme | |
Multi-step reaction with 7 steps 1.1: ethanol / 3 h / Inert atmosphere; Reflux 2.1: (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; triphenylborane / toluene / 0.17 h / 20 °C / Molecular sieve; Inert atmosphere 2.2: 19 h / -10 - 20 °C / Molecular sieve; Inert atmosphere 3.1: lithium borohydride / tetrahydrofuran / 50 °C / Inert atmosphere 3.2: 1 h / 20 °C / Inert atmosphere 4.1: diethylamino-sulfur trifluoride; triethylamine / dichloromethane / 8 h / -40 - 20 °C / Inert atmosphere 5.1: water; toluene-4-sulfonic acid / acetonitrile / 24 h / 40 °C / Inert atmosphere 5.2: Inert atmosphere 6.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / methanol; water / 6 h / 20 °C / 760.05 Torr 7.1: triethylamine / methanol / 3 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 7 steps 1.1: sodium hydroxide / dichloromethane; ethanol / 0 - 20 °C 1.2: 1 h / 20 °C / Cooling with ice 2.1: thionyl chloride / 8 h / 0 - 60 °C 2.2: 2 h / 20 - 60 °C 3.1: hydrogenchloride / water; methanol / 6 h / Reflux 3.2: 8 h / 0 - 60 °C 3.3: 6 h / 20 °C 4.1: sodium tetrahydroborate; methanol / 5 h / 0 - 20 °C 5.1: triethylamine; thionyl chloride / dichloromethane / 0 °C 5.2: 20 °C 6.1: triethylamine tris(hydrogen fluoride) / 1,2-dichloro-ethane / 8 h / 70 °C 6.2: 2 h / 0 - 20 °C 7.1: triethylamine / methanol / Heating View Scheme |
3-(4-methanesulfonyl-phenyl)-acrylic acid
Florfenicol
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 1.) SOCl2, 2.) NaBH4 / 1) reflux, 1 h; 2) CH2Cl2, EtOH, 10 deg C, 1 h 2: 82 percent / 4 Anstroem molecular sieves, diisopropyl L-tartrate, Ti(OPr-i)4, t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / 4 h / -20 °C 3: 1.) NaH, 2.) ZnCl2, 3.) 4 Angstroem molecular sieves / 1) THF, 5 deg C, 30 min; 2) THF, 5 deg C, 30 min; 3) THF, 55 deg C, 16 h 4: 1.) Et3N, MeSO2Cl, 2.) aq. NaOH / 1) pyridine, 5 deg C, 2 h; 2) pyridine, pH 12.5 5: CF3CHCF2NEt2 / CH2Cl2 / 2 h / 100 °C 6: KOAc / methanol; propan-2-ol; H2O / 3 h / Heating; pH 5 View Scheme |
(1R,2R)-2-amino-1-<4-(methylsulphonyl)phenyl>-1,3-propanediol
Florfenicol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 88 percent / conc. H2SO4 / propan-2-ol / 1) 70 deg C, 1.5-2 h; 2) 50 deg C, 14 h 2: CF3CHCF2NEt2 / CH2Cl2 / 2 h / 100 °C 3: KOAc / methanol; propan-2-ol; H2O / 3 h / Heating; pH 5 View Scheme | |
Multi-step reaction with 6 steps 1: K2CO3 / H2O / 1 h / Ambient temperature 2: EtONa / ethanol 3: 40 percent / (2-chloro-1,1,2-trifluoroethyl)diethylamine / acetonitrile / 1.) room temp., 1 h, 2.) reflux, 3 h 4: 1.) BuLi / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min; room temp., 1 h 5: 70 percent / KOH / methanol / 7 h / -30 °C 6: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h View Scheme | |
Multi-step reaction with 4 steps 1: 95 percent / K2CO3 / glycerol / 18 h / 115 °C 2: 95 percent Chromat. / (1,1,2,3,3,3-hexafluoropropyl)diethylamine (FPA) / CH2Cl2 / 2 h / 100 °C / 5171.5 Torr 3: 95 percent / 6 N HCl / 12 h / 100 - 105 °C 4: 84 percent / Et3N / methanol / 18 h / Ambient temperature View Scheme |
(E)-3-(4-(methylsulfonyl)phenyl)prop-2-en-1-ol
Florfenicol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 82 percent / 4 Anstroem molecular sieves, diisopropyl L-tartrate, Ti(OPr-i)4, t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / 4 h / -20 °C 2: 1.) NaH, 2.) ZnCl2, 3.) 4 Angstroem molecular sieves / 1) THF, 5 deg C, 30 min; 2) THF, 5 deg C, 30 min; 3) THF, 55 deg C, 16 h 3: 1.) Et3N, MeSO2Cl, 2.) aq. NaOH / 1) pyridine, 5 deg C, 2 h; 2) pyridine, pH 12.5 4: CF3CHCF2NEt2 / CH2Cl2 / 2 h / 100 °C 5: KOAc / methanol; propan-2-ol; H2O / 3 h / Heating; pH 5 View Scheme | |
Multi-step reaction with 10 steps 1: tert.-butylhydroperoxide; C3H7O(1-)*C34H32N2O4(2-)*V(3+) / dichloromethane; water / 72 h / 0 °C 2: N,N-dimethyl-formamide / 10 h / 20 °C 3: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C 4: triethylamine / dichloromethane / 2 h / 0 - 20 °C 5: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 8 h / 90 °C 6: potassium hydroxide / methanol; water / 1 h / Reflux; Inert atmosphere 7: palladium 10% on activated carbon; formic acid / methanol / 10 h / 20 °C / Inert atmosphere 8: hydrogenchloride / water; isopropyl alcohol / 16 h / 50 - 70 °C 9: Nonafluorobutanesulfonyl fluoride; triethylamine tris(hydrogen fluoride); triethylamine / tetrahydrofuran / 12 h / 20 °C 10: sodium acetate / water; isopropyl alcohol / 3 h / pH 5 / Reflux View Scheme |
Florfenicol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1.) NaH, 2.) ZnCl2, 3.) 4 Angstroem molecular sieves / 1) THF, 5 deg C, 30 min; 2) THF, 5 deg C, 30 min; 3) THF, 55 deg C, 16 h 2: 1.) Et3N, MeSO2Cl, 2.) aq. NaOH / 1) pyridine, 5 deg C, 2 h; 2) pyridine, pH 12.5 3: CF3CHCF2NEt2 / CH2Cl2 / 2 h / 100 °C 4: KOAc / methanol; propan-2-ol; H2O / 3 h / Heating; pH 5 View Scheme | |
Multi-step reaction with 9 steps 1: N,N-dimethyl-formamide / 10 h / 20 °C 2: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C 3: triethylamine / dichloromethane / 2 h / 0 - 20 °C 4: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 8 h / 90 °C 5: potassium hydroxide / methanol; water / 1 h / Reflux; Inert atmosphere 6: palladium 10% on activated carbon; formic acid / methanol / 10 h / 20 °C / Inert atmosphere 7: hydrogenchloride / water; isopropyl alcohol / 16 h / 50 - 70 °C 8: Nonafluorobutanesulfonyl fluoride; triethylamine tris(hydrogen fluoride); triethylamine / tetrahydrofuran / 12 h / 20 °C 9: sodium acetate / water; isopropyl alcohol / 3 h / pH 5 / Reflux View Scheme |
(3S,4R)-2-(dichloromethyl)-4,5-dihydro-α-[4-(methylsulfonyl)phenyl]oxazole-4-methanol
Florfenicol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) Et3N, MeSO2Cl, 2.) aq. NaOH / 1) pyridine, 5 deg C, 2 h; 2) pyridine, pH 12.5 2: CF3CHCF2NEt2 / CH2Cl2 / 2 h / 100 °C 3: KOAc / methanol; propan-2-ol; H2O / 3 h / Heating; pH 5 View Scheme |
Florfenicol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 27 percent Chromat. / hexadecyltributylphosphonium chloride, potassium fluoride hydrate / toluene; H2O / 7 h / Heating 2: 2N HCl / 6 h / Heating 3: Et3N / 3.5 h / Heating View Scheme |
Florfenicol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 92.8 percent / pyridine / 0 °C 2: 27 percent Chromat. / hexadecyltributylphosphonium chloride, potassium fluoride hydrate / toluene; H2O / 7 h / Heating 3: 2N HCl / 6 h / Heating 4: Et3N / 3.5 h / Heating View Scheme |
Florfenicol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 2N HCl / 6 h / Heating 2: Et3N / 3.5 h / Heating View Scheme |
(R*,R*)-(+)-thiomicamine
Florfenicol
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: K2CO3 / H2O / 1 h / Ambient temperature 2: t-BuOK / ethanol / 3 h / Heating 3: 81 percent / H2O2 / H2O / 20 h / 45 °C 4: 40 percent / (2-chloro-1,1,2-trifluoroethyl)diethylamine / acetonitrile / 1.) room temp., 1 h, 2.) reflux, 3 h 5: 1.) BuLi / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min; room temp., 1 h 6: 70 percent / KOH / methanol / 7 h / -30 °C 7: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h View Scheme | |
Multi-step reaction with 7 steps 1: K2CO3 / H2O / 1 h / Ambient temperature 2: t-BuOK / toluene / 3 h / Heating 3: 81 percent / H2O2 / H2O / 20 h / 45 °C 4: 40 percent / (2-chloro-1,1,2-trifluoroethyl)diethylamine / acetonitrile / 1.) room temp., 1 h, 2.) reflux, 3 h 5: 1.) BuLi / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min; room temp., 1 h 6: 70 percent / KOH / methanol / 7 h / -30 °C 7: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h View Scheme | |
Multi-step reaction with 4 steps 1: 1.) K2CO3, 2.) CH3CO3H / 1.) ethylene glycol, glycerol, 105 deg C, 18 h, 2.) AcOH, 20-25 deg C , 1 h 2: 95 percent Chromat. / (1,1,2,3,3,3-hexafluoropropyl)diethylamine (FPA) / CH2Cl2 / 2 h / 100 °C / 5171.5 Torr 3: 95 percent / 6 N HCl / 12 h / 100 - 105 °C 4: 84 percent / Et3N / methanol / 18 h / Ambient temperature View Scheme | |
Multi-step reaction with 4 steps 1: 1.) K2CO3, 2.) CH3CO3H / 1.) ethylene glycol, glycerol, 105 deg C, 18 h, 2.) AcOH, 20-25 deg C , 1 h 2: (2-chloro-1,1,2-trifluoroethyl)diethylamine (FAR) / CH2Cl2 / 5 h / 100 °C 3: 95 percent / 6 N HCl / 12 h / 100 - 105 °C 4: 84 percent / Et3N / methanol / 18 h / Ambient temperature View Scheme |
(4R,5R)-4-hydroxymethyl-5-<4-(methylthio)phenyl>-2-oxazolidinone
Florfenicol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 81 percent / H2O2 / H2O / 20 h / 45 °C 2: 40 percent / (2-chloro-1,1,2-trifluoroethyl)diethylamine / acetonitrile / 1.) room temp., 1 h, 2.) reflux, 3 h 3: 1.) BuLi / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min; room temp., 1 h 4: 70 percent / KOH / methanol / 7 h / -30 °C 5: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h View Scheme |
(1R,2R)-2-ethoxycarbonylamino-1-<4-(methylthio)phenyl>-1,3-propanediol
Florfenicol
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: t-BuOK / ethanol / 3 h / Heating 2: 81 percent / H2O2 / H2O / 20 h / 45 °C 3: 40 percent / (2-chloro-1,1,2-trifluoroethyl)diethylamine / acetonitrile / 1.) room temp., 1 h, 2.) reflux, 3 h 4: 1.) BuLi / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min; room temp., 1 h 5: 70 percent / KOH / methanol / 7 h / -30 °C 6: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h View Scheme | |
Multi-step reaction with 6 steps 1: t-BuOK / toluene / 3 h / Heating 2: 81 percent / H2O2 / H2O / 20 h / 45 °C 3: 40 percent / (2-chloro-1,1,2-trifluoroethyl)diethylamine / acetonitrile / 1.) room temp., 1 h, 2.) reflux, 3 h 4: 1.) BuLi / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min; room temp., 1 h 5: 70 percent / KOH / methanol / 7 h / -30 °C 6: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h View Scheme |
(4R,5R)-4-hydroxymethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone
Florfenicol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 40 percent / (2-chloro-1,1,2-trifluoroethyl)diethylamine / acetonitrile / 1.) room temp., 1 h, 2.) reflux, 3 h 2: 1.) BuLi / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min; room temp., 1 h 3: 70 percent / KOH / methanol / 7 h / -30 °C 4: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h View Scheme | |
Multi-step reaction with 3 steps 1: hexafluoropropene-diethylamine adduct / dichloromethane / 1 h / 105 - 110 °C / Autoclave 2: hydrogenchloride / 1 h / Reflux 3: triethylamine / methanol / 20 °C View Scheme |
(4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone
Florfenicol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) BuLi / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min; room temp., 1 h 2: 70 percent / KOH / methanol / 7 h / -30 °C 3: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h View Scheme | |
Multi-step reaction with 2 steps 1: hydrogenchloride / 1 h / Reflux 2: triethylamine / methanol / 20 °C View Scheme |
(1R,2R)-2-ethoxycarbonylamino-1-<4-(methylsulphonyl)phenyl>-1,3-propanediol
Florfenicol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: EtONa / ethanol 2: 40 percent / (2-chloro-1,1,2-trifluoroethyl)diethylamine / acetonitrile / 1.) room temp., 1 h, 2.) reflux, 3 h 3: 1.) BuLi / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min; room temp., 1 h 4: 70 percent / KOH / methanol / 7 h / -30 °C 5: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h View Scheme |
(4S,5R)-N-(2,3-dimethylbenzoyl)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone
Florfenicol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / KOH / methanol / 7 h / -30 °C 2: 1.) 6N HCl, 2.) Et3N / 1.) 120 deg C, 5 h, 2.) 80 deg C, 2 h View Scheme |
succinic acid
Florfenicol
sodium 4-((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propoxy)-4-oxobutanoate
Conditions | Yield |
---|---|
Stage #1: succinic acid; Florfenicol With triethylamine In ethyl acetate at 20℃; for 1h; Stage #2: With sodium hydrogencarbonate In ethyl acetate at 0 - 5℃; for 2h; Solvent; | 97.8% |
N-benzyloxycarbonyl-L-alanyl chloride
Florfenicol
Conditions | Yield |
---|---|
With triethylamine In 1,2-dichloro-ethane at 20 - 90℃; for 10h; Reagent/catalyst; Solvent; Temperature; | 94.3% |
Florfenicol
methyl chloroformate
Conditions | Yield |
---|---|
With dmap; triethylamine In tetrahydrofuran at 0℃; | 93% |
Conditions | Yield |
---|---|
With pyridine In chloroform at 20℃; for 8h; Reflux; | 89.64% |
succinic acid anhydride
Florfenicol
4-((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propoxy)-4-oxobutanoic acid
Conditions | Yield |
---|---|
With dmap In acetone at 60℃; for 4h; | 88.1% |
With dmap In acetone at 40 - 70℃; |
Conditions | Yield |
---|---|
With pyridine; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 10h; Reflux; | 83.29% |
Florfenicol
bis((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propyl) hydrogen phosphate
Conditions | Yield |
---|---|
Stage #1: Florfenicol With pyridine; trichlorophosphate In acetonitrile at 0 - 25℃; for 12.5h; Stage #2: With water In acetonitrile at 0 - 25℃; for 8.16667h; Reagent/catalyst; Solvent; | 80.72% |
(S)-benzyloxycarbonyl-proline acid chloride
Florfenicol
Conditions | Yield |
---|---|
With pyridine In chloroform at 20℃; for 10h; Reflux; | 70.39% |
ethylenebis(chloroformate)
Florfenicol
Conditions | Yield |
---|---|
With dmap; triethylamine In tetrahydrofuran at 0 - 20℃; | 62% |
Florfenicol
2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside
Conditions | Yield |
---|---|
Stage #1: 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside With trifluoromethylsulfonic anhydride; beta-pinene In dichloromethane at -50℃; for 0.75h; Stage #2: Florfenicol In dichloromethane at -50 - 20℃; for 18h; stereoselective reaction; | 55% |
N,O-bis-(trimethylsilyl)-acetamide
Florfenicol
Conditions | Yield |
---|---|
In acetonitrile at 50℃; for 0.166667h; |
Molecular Structure of Florfenicol (CAS NO.73231-34-2):
IUPAC Name: 2,2-dichloro-N-[(1R,2S)-3-fluoro-1-hydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide
Empirical Formula: C12H14Cl2FNO4S
Molecular Weight: 358.21
H bond acceptors: 5
H bond donors: 2
Freely Rotating Bonds: 7
Polar Surface Area: 72.06 Å2
Index of Refraction: 1.548
Molar Refractivity: 78.36 cm3
Molar Volume: 246.7 cm3
Surface Tension: 49.1 dyne/cm
Density: 1.451 g/cm3
Flash Point: 327.3 °C
Enthalpy of Vaporization: 96.27 kJ/mol
Boiling Point: 617.5 °C at 760 mmHg
Vapour Pressure: 4.16E-16 mmHg at 25°C
Melting point: 153 °C
Storage temp: 0-6°C
Product Categories: Feed additives; Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds
Synonyms 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(methylsulfonyl)phenyl)propan-2-yl)ethanamide
InChI
InChI=1/C12H14Cl2FNO4S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-15)16-12(18)11(13)14/h2-5,9-11,17H,6H2,1H3,(H,16,18)/t9-,10-/m1/s1
Smiles
c1cc([C@H]([C@@H](CF)NC(C(Cl)Cl)=O)O)ccc1S(C)(=O)=O
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 100mg/kg (100mg/kg) | Drugs of the Future. Vol. 7, Pg. 172, 1982. |
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 3
Florfenicol (CAS NO.73231-34-2) is a fluorinated synthetic analog of thiamphenicol. In the United States, florfenicol is currently indicated for the treatment of bovine respiratory disease . Florfenicol is a bacteriostatic antibiotic that inhibits protein synthesis by binding to ribosomal subunits of susceptible bacteria, leading to the inhibition of peptidyl transferase and thereby preventing the transfer of amino acids to growing peptide chains and subsequent protein formation.
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