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Florfenicol Manufacturer/High quality/Best price/In stock
Cas No: 73231-34-2
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
Florfenicol
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USD $ 75.0-80.0 / Kilogram 25 Kilogram 50 Metric Ton/Day Antimex Chemical Limied Contact Supplier
Florfenicol
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USD $ 99.0-99.0 / Kilogram 100 Kilogram 100 Metric Ton/Year Hangzhou Deli Chemical Co.,Ltd. Contact Supplier
Florfenicol
Cas No: 73231-34-2
No Data 100 Gram 100 Kilogram/Month ShangHai Jin Dun Industrial CO., LTD Contact Supplier
Florfenicol
Cas No: 73231-34-2
USD $ 51.0-55.0 / Kilogram 50 Kilogram 300 Metric Ton/Month Arshine Pharmaceutical Co., Limited Contact Supplier
APIs 99% White Powder CAS 73231-34-2 Florfenicol
Cas No: 73231-34-2
USD $ 9.0-10.0 / Kilogram 1 Kilogram 500 Metric Ton/Month Shanlong Biotechnology (hebei) Co., Ltd. Contact Supplier
Florfenicol CP2010 GMP China VETERINARY
Cas No: 73231-34-2
No Data 100 Gram Metric Ton/Day Hangzhou Dawn Ray Pharmaceutical Co.,Ltd Contact Supplier
High quality 2,2-Dichloro-N-[(1R,2S)-3-Fluoro-1-Hydroxy-1-(4-Methylsulfonylphenyl)Propan-2-Yl]Acetamide supplier in China
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No Data No Data Metric Ton/Day Simagchem Corporation Contact Supplier
CAS:73231-34-2 Florfenicol
Cas No: 73231-34-2
No Data 5 Gram 100 Kilogram/Year Kono Chem Co.,Ltd Contact Supplier
Lowest price and high quality florfenicol
Cas No: 73231-34-2
USD $ 1.0-1.0 / Gram 1 Gram 10 Metric Ton/Month Hebei yanxi chemical co.,LTD. Contact Supplier

73231-34-2 Usage

Uses

Florfenicol is synthesised from thiamphenicol by replacing the 3-hydroxy group with fluorine, first synthesised at Schering in 1980. By replacing the hydroxy group, it was rationalised that chloramphenicol resistance via chloramphenicol acetyltransferase could be eliminated. Florfenicol is a broad spectrum antibiotic with good activity against Gram negative and anaerobic bacteria. Florfenicol acts by binding to the 23S sub-unit of the 50S ribosome, inhibiting protein synthesis. Florfenicol has been extensively studied with over 400 literature citations.

Pharmacological effects

Florfenicol binds tightly with the 50S subunit of the bacterial ribosome and block the transpeptidation reaction mediated by peptidyl transferase, and thereby suppressing the elongation process of the peptide chain; meanwhile selectively acts on the bacterial 70S ribosome receptors and changes, interferes with the function of peptidyl transferase enzyme. Therefore, it interferes with the bacterial protein synthesis based on dual mechanism.

Veterinary antibiotics

Florfenicol is currently a commonly used veterinary antibiotic with a broad antibacterial spectrum and a strong antibacterial effect as well as a low the minimum inhibitory concentration (MIC). The antibacterial of florfenicol is about 15-20 times as high as that of chloramphenicol and the thiamphenicol. After administration through feed for 60 minutes, the drug concentration in the tissue can reach peak which can quickly control the disease with having characteristics such as being safe, non-toxic, no residue, and no risk for triggering aplastic anemia. Therefore, it is quite suitable for large-scale farms application. It is mainly used for the treatment of bovine respiratory disease caused by Pasteurella and Haemophilus. It has good efficacy in treating the cattle footrot disease cause by Fusobacterium, and can be also used for treating the infection diseases of pigs and chickens caused by sensitive strains as well as the bacterial disease of fish.
It is not easy for bacteria to evolve resistance against florfenicol: Because it has a fluorine atom which replaces the hydroxyl group on the molecular structure of thiamphenicol, thus effectively solving the drug resistant issue of chloramphenicol, and thiamphenicol. Bacteria which are resistant to thiamphenicol, chloramphenicol, amoxicillin, and quinolone remain sensitive to the chemicals.
Since chloramphenicol can result in severe adverse reactions such as aplastic anemia and immune suppression, it is banned from being applied in food animal production. Studies have demonstrated that: the major group in the chemical structure of chloramphenicol which causes aplastic anemia is para-nitro in the aromatic ring. Instead, florfenicol has the CH3SO4 which replaces the NO2 groups so that its chemical structure has been changed. In this case, its application to animal will not cause any adverse reactions such as aplastic anemia. Therefore, it is approved for application in more than a dozen of countries such as Japan, Mexico and China. Florfenicol is characterized by: a broad spectrum antibiotic; Salmonella, Escherichia coli, Proteus, Haemophilus, Actinobacillus pleuropneumoniae, Mycoplasma hyopneumoniae, Streptococcus Suis, swine Pasteurella, Bordetclla bronchiseptica, and Staphylococcus aureus are all sensitive to it. The drug is easy for absorbing and is widely distributed in the body and is quick-acting and long-acting formulations with no potential risk of causing aplastic anemia risks and thus having a better security. In addition, it has an affordable price which is cheaper than other drugs for prevention and treatment of respiratory diseases such as tiamulin, tilmicosin, and azithromycin. The cost of medication is easy for users to accept. Because of all these excellent characteristics, domestic florfenicol is widely applied and has currently become the first-choice drug for prevention and treatment of livestock respiratory diseases and gastrointestinal bacterial infection diseases.
Florfenicol is not suitable to be applied in combination with quinolones, penicillins, and cephalosporins, and it has no compatibility with ampicillin, sulfonamides, and furans.
The above information is edited by the Chemicalbook of Dai Xiongfeng.

Uses

Antibacterial;Protein synthesis inhibitor

Uses

It is a kind of antibacterial drug. It is used as the veterinary antimicrobial drugs for treating bacterial diseases of pigs, chickens and fish. It has good efficacy in treating the infection disease of pigs, chickens and fish induced by sensitive bacteria, especially for treating respiratory infections and intestinal infections.

Chemical Properties

White Crystalline Powder

Uses

Fluorinated derivative of thiamphenicol. Inhibits bacterial protein synthesis by binding to ribosome 50S and 70S subunits. An antibacterial

Indications

Florfenicol can strongly interfere with the bacterial protein synthesis. It has a rapid absorption rate and is widely distributed in the body; it has long half-life without side effects such as aplastic anemia; not easy for bacteria to evolve drug resistance, and has no cross-resistance.
Florfenicol can be used for the treatment of the systemic infection of livestock and aquatic animals, and has significant efficacy on treating respiratory infections and intestinal infections.
Poultry: Escherichia coli disease, salmonellosis, infectious rhinitis, chronic respiratory disease, duck plague and other kinds of mixed infections caused by susceptible strains.
Animals: Mixed infections such as infectious pleurisy, asthma, streptococcal disease, Escherichia coli disease, salmonellosis, contagious pleuropneumonia, enzootic pneumonia, paratyphoid piglets yellow white diarrhea, edema disease, atrophic rhinitis, lung epidemic, red white diarrhea piglets, and agalactia syndrome occurred in animals such as pigs, cows, and sheep.
Crab: appendages ulcer disease, yellow gills, rotten gill, red legs and red fluorescent body inflammatory disease syndrome.
Turtle: red neck disease, furunculosis, shot-hole disease, skin fester disease, inflammatory bowel disease, mumps, and bacterial sepsis.
Frogs: cataract syndrome, ascites disease, sepsis, enteritis.
Fish: enteritis disease, ascites disease, vibriosis, Edward coli disease.
Eel: debonding septicemia (unique effect), Edward coli disease, red skin disease, inflammatory bowel disease.

Uses

Florfenicol is a fluorinated derivative of thiamphenicol. Florfenicol inhibits bacterial protein synthesis by binding to ribosome 50S and 70S subunits. Florfenicol is used as an antibacterial.

Definition

ChEBI: A carboxamide that is the N-dichloroacetyl derivative of (1R,2S)-2-amino-3-fluoro-1-[4-(methanesulfonyl)phenyl]propan-1-ol. A synthetic veterinary antibiotic that is used for treatment of bovine respirat ry disease and foot rot; also used in aquaculture.
InChI:InChI=1/C12H14Cl2FNO2S/c1-19-8-4-2-7(3-5-8)10(17)9(6-15)16-12(18)11(13)14/h2-5,9-11,17H,6H2,1H3,(H,16,18)

73231-34-2 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (F0811)  Florfenicol  >98.0%(HPLC)(N) 73231-34-2 5g 3,250.00CNY Detail
TCI America (F0811)  Florfenicol  >98.0%(HPLC)(N) 73231-34-2 1g 740.00CNY Detail

73231-34-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name florfenicol

1.2 Other means of identification

Product number -
Other names Florfenicol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:73231-34-2 SDS

73231-34-2Synthetic route

(4S,5R)-2-dichloromethyl-4-fluoromethyl-4,5-dihydro-5-(4-(methylsulfonyl)phenyl)oxazoline
143026-79-3

(4S,5R)-2-dichloromethyl-4-fluoromethyl-4,5-dihydro-5-(4-(methylsulfonyl)phenyl)oxazoline

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
116-54-1

dichloroacetic acid methyl ester

(1R,2S)-2-amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol
76639-93-5, 105182-37-4, 118015-48-8

(1R,2S)-2-amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
895571-10-5

(1R,2S)-1-(4-methylsulfonylphenyl)-2-benzylamino-3-fluoro-1-propanol

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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%
(1R,2S)-2-amino-3-fluoro-1-(4-methylsulphonylphenyl)-1-propanol hydrochloride

(1R,2S)-2-amino-3-fluoro-1-(4-methylsulphonylphenyl)-1-propanol hydrochloride

dichloroacetic acid methyl ester
116-54-1

dichloroacetic acid methyl ester

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
C12H12Cl2FNO3S

C12H12Cl2FNO3S

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
126813-11-4

D-threo-2-(dichloromethyl)-5-(4-methanesulfonylphenyl)-4,5-dihydro-1,3-oxazol-4-yl methanol

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
116-54-1

dichloroacetic acid methyl ester

(1R,2S)-3-fluoro-1-(4-(methylsulfonyl)phenyl)-2-nitropropan-1-ol

(1R,2S)-3-fluoro-1-(4-(methylsulfonyl)phenyl)-2-nitropropan-1-ol

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
96795-01-6

C13H15Cl2NO6S2

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
With triethylamine tris(hydrogen fluoride) In acetonitrile for 10h; Reflux;65%
dichloroacetic acid methyl ester
116-54-1

dichloroacetic acid methyl ester

(4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone
108656-28-6

(4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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%
2,2-dichloro-N-{(4R,5R)-4-[4-(methylsulfonyl)phenyl]-2,2-dioxido-1,3,2-dioxathian-5-yl}acetamide

2,2-dichloro-N-{(4R,5R)-4-[4-(methylsulfonyl)phenyl]-2,2-dioxido-1,3,2-dioxathian-5-yl}acetamide

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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%
florfenicol phosphate
857859-74-6

florfenicol phosphate

A

C12H14Cl2NO7PS

C12H14Cl2NO7PS

B

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
116-54-1

dichloroacetic acid methyl ester

(1R,2S)-2-(2,3-dimethylbenzoyl)amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol
108656-27-5

(1R,2S)-2-(2,3-dimethylbenzoyl)amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol

A

thiamphenicol
15318-45-3

thiamphenicol

B

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
4302-89-0

(1R,2R)-2-(2,2-dichloro-acetylamino)-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multistep reaction;
dichloroacetic acid methyl ester
116-54-1

dichloroacetic acid methyl ester

(1R,2S)-2-amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol
76639-93-5, 105182-37-4, 118015-48-8

(1R,2S)-2-amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol

A

(1R,2S)-2-Dichloroacetamido-3-Fluoro-1-[4-(Methylsulfonyl)Phenyl]-1-Propanol(Florfenicol)

(1R,2S)-2-Dichloroacetamido-3-Fluoro-1-[4-(Methylsulfonyl)Phenyl]-1-Propanol(Florfenicol)

B

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
In methanol; water; toluene
para-methanesulfonylbenzaldehyde
5398-77-6

para-methanesulfonylbenzaldehyde

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
5345-30-2, 88899-85-8

3-(4-methanesulfonyl-phenyl)-acrylic acid

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
51458-28-7

(1R,2R)-2-amino-1-<4-(methylsulphonyl)phenyl>-1,3-propanediol

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
125872-64-2

(E)-3-(4-(methylsulfonyl)phenyl)prop-2-en-1-ol

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
(S,S)-3-[4-(methylsulfonyl)phenyl]-2,3-epoxypropyl alcohol

(S,S)-3-[4-(methylsulfonyl)phenyl]-2,3-epoxypropyl alcohol

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
157142-64-8

(3S,4R)-2-(dichloromethyl)-4,5-dihydro-α-[4-(methylsulfonyl)phenyl]oxazole-4-methanol

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
(2R,3S,9bRS)-3-(mesyloxymethyl)-2-<4-(methylsulphonyl)phenyl>-2,3-dihydrooxazolo<2,3-a>isoindol-5(9bH)-one

(2R,3S,9bRS)-3-(mesyloxymethyl)-2-<4-(methylsulphonyl)phenyl>-2,3-dihydrooxazolo<2,3-a>isoindol-5(9bH)-one

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
(2R,3R,9bRS)-3-hydroxymethyl-2-<4-(methylsulphonyl)phenyl>-2,3-dihydrooxazolo<2,3-a>isoindol-5(9bH)-one

(2R,3R,9bRS)-3-hydroxymethyl-2-<4-(methylsulphonyl)phenyl>-2,3-dihydrooxazolo<2,3-a>isoindol-5(9bH)-one

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
(2R,3S,9bRS)-3-fluoromethyl-2-<4-(methylsulphonyl)phenyl>-2,3-dihydrooxazolo<2,3-a>isoindol-5(9bH)-one

(2R,3S,9bRS)-3-fluoromethyl-2-<4-(methylsulphonyl)phenyl>-2,3-dihydrooxazolo<2,3-a>isoindol-5(9bH)-one

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2N HCl / 6 h / Heating
2: Et3N / 3.5 h / Heating
View Scheme
(R*,R*)-(+)-thiomicamine
23150-35-8

(R*,R*)-(+)-thiomicamine

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
96795-21-0

(4R,5R)-4-hydroxymethyl-5-<4-(methylthio)phenyl>-2-oxazolidinone

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
96795-20-9

(1R,2R)-2-ethoxycarbonylamino-1-<4-(methylthio)phenyl>-1,3-propanediol

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
96795-22-1

(4R,5R)-4-hydroxymethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
108656-28-6

(4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
108656-26-4

(1R,2R)-2-ethoxycarbonylamino-1-<4-(methylsulphonyl)phenyl>-1,3-propanediol

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
108656-29-7

(4S,5R)-N-(2,3-dimethylbenzoyl)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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
110-15-6

succinic acid

Florfenicol
73231-34-2

Florfenicol

sodium 4-((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propoxy)-4-oxobutanoate
1073342-32-1

sodium 4-((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propoxy)-4-oxobutanoate

Conditions
ConditionsYield
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
49760-60-3

N-benzyloxycarbonyl-L-alanyl chloride

Florfenicol
73231-34-2

Florfenicol

florfenicol-N-Cbz-L-alanine ester

florfenicol-N-Cbz-L-alanine ester

Conditions
ConditionsYield
With triethylamine In 1,2-dichloro-ethane at 20 - 90℃; for 10h; Reagent/catalyst; Solvent; Temperature;94.3%
Florfenicol
73231-34-2

Florfenicol

methyl chloroformate
79-22-1

methyl chloroformate

(1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propyl methyl carbonate

(1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propyl methyl carbonate

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 0℃;93%
N-Z-Leucine chloride
87052-59-3

N-Z-Leucine chloride

Florfenicol
73231-34-2

Florfenicol

florfenicol-N-Cbz-L-leucine ester

florfenicol-N-Cbz-L-leucine ester

Conditions
ConditionsYield
With pyridine In chloroform at 20℃; for 8h; Reflux;89.64%
succinic acid anhydride
108-30-5

succinic acid anhydride

Florfenicol
73231-34-2

Florfenicol

4-((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propoxy)-4-oxobutanoic acid
1073342-33-2

4-((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propoxy)-4-oxobutanoic acid

Conditions
ConditionsYield
With dmap In acetone at 60℃; for 4h;88.1%
With dmap In acetone at 40 - 70℃;
Z-(L)-Val-Cl
87052-60-6

Z-(L)-Val-Cl

Florfenicol
73231-34-2

Florfenicol

florfenicol-N-Cbz-L-valine ester

florfenicol-N-Cbz-L-valine ester

Conditions
ConditionsYield
With pyridine; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 10h; Reflux;83.29%
Florfenicol
73231-34-2

Florfenicol

bis((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propyl) hydrogen phosphate
1450713-53-7

bis((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propyl) hydrogen phosphate

Conditions
ConditionsYield
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
61350-60-5, 61350-62-7, 89705-40-8, 106709-50-6

(S)-benzyloxycarbonyl-proline acid chloride

Florfenicol
73231-34-2

Florfenicol

florfenicol-N-Cbz-L-proline ester

florfenicol-N-Cbz-L-proline ester

Conditions
ConditionsYield
With pyridine In chloroform at 20℃; for 10h; Reflux;70.39%
ethylenebis(chloroformate)
124-05-0

ethylenebis(chloroformate)

Florfenicol
73231-34-2

Florfenicol

bis((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propyl)ethane-1,2-diyl dicarbonate

bis((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-(4-(methylsulfonyl)phenyl)propyl)ethane-1,2-diyl dicarbonate

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 0 - 20℃;62%
Florfenicol
73231-34-2

Florfenicol

2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside
148926-02-7

2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside

2,2-dichloro-N-[(1R,2S)-3-fluoro-1-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyloxy)-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide

2,2-dichloro-N-[(1R,2S)-3-fluoro-1-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyloxy)-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide

Conditions
ConditionsYield
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
10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

Florfenicol
73231-34-2

Florfenicol

2,2-Dichloro-N-[(1S,2R)-1-fluoromethyl-2-(4-methanesulfonyl-phenyl)-2-trimethylsilanyloxy-ethyl]-acetamide

2,2-Dichloro-N-[(1S,2R)-1-fluoromethyl-2-(4-methanesulfonyl-phenyl)-2-trimethylsilanyloxy-ethyl]-acetamide

Conditions
ConditionsYield
In acetonitrile at 50℃; for 0.166667h;

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