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TIANFU-CHEM (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acidAppearance:white powder Storage:room temperature Package:200KG Application:Industrial Grade Transportation:By sea , by ai
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Conditions | Yield |
---|---|
Stage #1: 7-Aminocephalosporanic acid With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane at 25 - 30℃; Inert atmosphere; Stage #2: 2-thienylacetic acid chloride In dichloromethane at 10℃; for 1h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere; | 92% |
With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile Inert atmosphere; | 85% |
With tetrabutylammomium bromide; sodium hydrogencarbonate In dichloromethane; water at -5 - 0℃; Temperature; |
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 30℃; for 2h; Time; Reagent/catalyst; Green chemistry; | 85% |
Thiophene-2-acetic acid
1-methanesulfonyloxy-1,2,3-benzotriazole
cephalothin
Conditions | Yield |
---|---|
With sodium acetate; acetic acid; triethylamine In dichloromethane | 70% |
3-(trimethylsiloxy)-8-oxo-7-(2-(2-thienyl) acetamido)-5-thiazabicyclo [4.2.0]Carboxylic acid
cephalothin
Conditions | Yield |
---|---|
With water; hydrogen cation Yield given; |
2,2,2-trichloroethyl (6R,7R)-3-acetoxymethyl-7-(thien-2-ylacetamido)ceph-3-em-4-carboxylate
cephalothin
Conditions | Yield |
---|---|
With Deacidite FF ion-exchange resin; zinc(II) chloride; zinc 1.) formic acid, RT, 5 h; Multistep reaction; |
Conditions | Yield |
---|---|
With potassium chloride In water at 30℃; Equilibrium constant; |
2-thienylacetic acid chloride
cephalothin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 92 percent / ethylene oxide / CH2Cl2 / 0.07 h 2: 68 percent / acetic acid / dimethylformamide / 3 h / 22 °C 3: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 4: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme | |
Multi-step reaction with 5 steps 1: 1.) phosphorus oxychloride; 2.) dimethylacetamide / 1.) MeOH, 45-55 deg C; 2.) CH2Cl2, 0-5 deg C, 45 min 2: 66 percent / sodium iodide / acetone / 1.5 h 3: 50 percent / acetic acid / dimethylformamide / 3 h / 22 °C 4: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 5: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 46.3 percent / N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 1 h / 20 °C 2: 66 percent / sodium iodide / acetone / 1.5 h 3: 50 percent / acetic acid / dimethylformamide / 3 h / 22 °C 4: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 5: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme |
2,2,2-trichloroethyl (1S,6R,7R)-3-chloromethyl-7-(thien-2-ylacetamido)ceph-3-em-4-carboxylate 1-oxide
cephalothin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 66 percent / sodium iodide / acetone / 1.5 h 2: 50 percent / acetic acid / dimethylformamide / 3 h / 22 °C 3: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 4: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme |
2,2,2-trichloroethyl (1S,6R,7R)-3-bromomethyl-7-(thien-2-ylacetamido)ceph-3-em-4-carboxylate 1-oxide
cephalothin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 68 percent / acetic acid / dimethylformamide / 3 h / 22 °C 2: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 3: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme |
2,2,2-trichloroethyl (1S,6R,7R)-3-iodomethyl-7-(thien-2-ylacetamido)ceph-3-em-4-carboxylate 1-oxide
cephalothin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 50 percent / acetic acid / dimethylformamide / 3 h / 22 °C 2: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 3: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme |
2,2,2-trichloroethyl (1S,6R,7R)-3-acetoxymethyl-7-(thien-2-ylacetamido)ceph-3-em-4-carboxylate 1-oxide
cephalothin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 2: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme |
2,2,2-trichloroethyl (1S,6R,7R)-7-amino-3-bromomethylceph-3-em-4-carboxylate 1-oxide hydrobromide
cephalothin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 92 percent / ethylene oxide / CH2Cl2 / 0.07 h 2: 68 percent / acetic acid / dimethylformamide / 3 h / 22 °C 3: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 4: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme |
2,2,2-trichloroethyl (1S,6R,7R)-7-amino-3-chloromethylceph-3-em-4-carboxylate 1-oxide
cephalothin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 46.3 percent / N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 1 h / 20 °C 2: 66 percent / sodium iodide / acetone / 1.5 h 3: 50 percent / acetic acid / dimethylformamide / 3 h / 22 °C 4: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 5: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme |
2,2,2-trichloroethyl (1S,6R,7R)-3-bromomethyl-7-formamidoceph-3-em-4-carboxylate 1-oxide
cephalothin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 1.) phosphorus oxychloride; 2.) dimethylacetamide / 1.) MeOH, 45-55 deg C; 2.) CH2Cl2, 0-5 deg C, 45 min 2: 66 percent / sodium iodide / acetone / 1.5 h 3: 50 percent / acetic acid / dimethylformamide / 3 h / 22 °C 4: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 5: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme | |
Multi-step reaction with 4 steps 1: 1.) phosphorus oxychloride; 2.) dimethylacetamide / 1.) MeOH, 45-55 deg C; 2.) CH2Cl2, 0-5 deg C, 45 min 2: 68 percent / acetic acid / dimethylformamide / 3 h / 22 °C 3: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 4: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme | |
Multi-step reaction with 5 steps 1: 98 percent / phosphorus tribromide / methanol; diethyl ether / 1.17 h / 0 - 10 °C 2: 92 percent / ethylene oxide / CH2Cl2 / 0.07 h 3: 68 percent / acetic acid / dimethylformamide / 3 h / 22 °C 4: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 5: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme | |
Multi-step reaction with 6 steps 1: 46.2 percent / conc. hydrochloric acid / tetrahydrofuran / 30 h / 6 °C 2: 46.3 percent / N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 1 h / 20 °C 3: 66 percent / sodium iodide / acetone / 1.5 h 4: 50 percent / acetic acid / dimethylformamide / 3 h / 22 °C 5: 65 percent / potassium iodide, acetyl chloride / acetic acid / 0.17 h / 20 °C 6: 1.) Zn, ZnCl2; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, RT, 5 h View Scheme |
p-methoxybenzyl 7β-(2-thienylacetamido)-3-(acetoxymethyl)-3-cephem-4-carboxylate
cephalothin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CH2Cl2 / 0.25 h / 20 °C 2: H2O, H(1+) View Scheme |
(6R,7R)-3-Acetoxymethyl-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methyl-benzyl ester
cephalothin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CDCl3 / 0.25 h / 20 °C 2: H2O, H(1+) View Scheme |
(6R,7R)-3-Acetoxymethyl-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2-methyl-benzyl ester
cephalothin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CDCl3 / 0.25 h / 20 °C 2: H2O, H(1+) View Scheme |
(6R)-3-acetoxymethyl-8-oxo-7t-(2-thiophen-2-yl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
cephalothin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CH2Cl2 / 0.25 h / 20 °C 2: H2O, H(1+) View Scheme |
2-thienylacetic acid chloride
2-diethylamino-1,3,2-dioxaphospholane
cephalothin
Conditions | Yield |
---|---|
With sodium hydroxide; chloro-trimethyl-silane In water; ethyl acetate; acetonitrile |
2-thienylacetic acid chloride
2-chloro-[1,3,2]dioxaborolane
7-Aminocephalosporanic acid
cephalothin
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; triethylamine In dichloromethane; water; acetone |
Conditions | Yield |
---|---|
With ammonium hydroxide; penicillin G amidase In water at 20℃; pH=6.5 - 7; Enzymatic reaction; |
2-thiopheneacetyl N-hydroxysuccinimide ester
7-Aminocephalosporanic acid
cephalothin
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane at 15 - 25℃; for 1h; Solvent; Temperature; Concentration; Irradiation; | 154 g |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In methanol; ethanol; Isopropyl acetate; water; ethyl acetate | 19.4% |
Conditions | Yield |
---|---|
With sodium 2-ethylhexanoic acid In acetone | 26% |
2,2,2-trichloroethyl glycinate*HBr
cephalothin
{[(6R,7R)-3-Acetoxymethyl-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carbonyl]-amino}-acetic acid 2,2,2-trichloro-ethyl ester
Conditions | Yield |
---|---|
With triethylamine; diisopropyl-carbodiimide In dichloromethane | 28% |
H2N-TrpOTce
cephalothin
(S)-2-{[(6R,7R)-3-Acetoxymethyl-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carbonyl]-amino}-3-(1H-indol-3-yl)-propionic acid 2,2,2-trichloro-ethyl ester
Conditions | Yield |
---|---|
With methyl(diethylamino)acetylene In dichloromethane | 31% |
1-methyl-5-mercaptotetrazole
cephalothin
Conditions | Yield |
---|---|
In acetic acid | 31% |
2-mercapto-5-methyl-1,3,4-thiadiazole
cephalothin
Conditions | Yield |
---|---|
In acetonitrile | 33.9% |
N-(2-hydroxyethyl)nicotinamide
cephalothin
B
2-<(3-pyridinylcarbonyl)amino>ethyl 7-(2-thienylacetamido)cephalosporante Δ3
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide at 20 - 25℃; for 20h; | A 17.9% B 35.9% |
cephalothin
Conditions | Yield |
---|---|
In hexane; ethyl acetate; acetonitrile | 38% |
Conditions | Yield |
---|---|
With 6,6′-[(3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(di-benzo[d,f][1,3,2]dioxaphosphepin); bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 60℃; for 5h; Tsuji-Trost Allylation; Schlenk technique; regioselective reaction; | 39% |
vinyldiazomethane
acetonitrile
cephalothin
A
allyl 7β-(2-(thien-2-yl)acetamido)-3-(acetoxymethyl)-3-cephem-4-carboxylate
Conditions | Yield |
---|---|
In diethyl ether | A 40% B 36% |
Conditions | Yield |
---|---|
With 6,6′-[(3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(di-benzo[d,f][1,3,2]dioxaphosphepin); bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 40℃; for 7h; Tsuji-Trost Allylation; Schlenk technique; regioselective reaction; | 41% |
Conditions | Yield |
---|---|
With methanesulfonic acid; sodium hydrogencarbonate In water; ethyl acetate; butanone | 41.6% |
cephalothin
Conditions | Yield |
---|---|
With sodium chloride; sodium hydrogencarbonate In 1,1,2-trichloroethane; ethyl acetate | 48% |
5-[(tetrazol-1-yl)methyl]-1,3,4-thiadiazole-2-thiol
cephalothin
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In acetic acid for 0.025h; Condensation; microwave irradiation; | 51% |
5-[(quinolin-8-yloxy)methyl]-1,3,4-thiadiazole-2-thiol
cephalothin
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In acetic acid for 0.0166667h; Condensation; microwave irradiation; | 53% |
5-[(5-methyl-1,3,4-thiadiazol-2-ylthio)methyl]-1,3,4-thiadiazole-2-thiol
cephalothin
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In acetic acid for 0.0166667h; Condensation; microwave irradiation; | 54% |
H2N-OTroc-TyrOTce
cephalothin
(S)-2-{[(6R,7R)-3-Acetoxymethyl-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carbonyl]-amino}-3-[4-(2,2,2-trichloro-ethoxycarbonyloxy)-phenyl]-propionic acid 2,2,2-trichloro-ethyl ester
Conditions | Yield |
---|---|
With methyl(diethylamino)acetylene In dichloromethane | 55% |
Conditions | Yield |
---|---|
In diethyl ether; nitromethane; ethyl acetate | 56.2% |
Conditions | Yield |
---|---|
With 6,6′-[(3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(di-benzo[d,f][1,3,2]dioxaphosphepin); bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 40℃; for 7h; Tsuji-Trost Allylation; Schlenk technique; regioselective reaction; | 58% |
5-[(4-methylquinolin-2-yloxy)methyl]-1,3,4-thiadiazole-2-thiol
cephalothin
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In acetic acid for 0.0333333h; Condensation; microwave irradiation; | 59% |
thioacetic acid
cephalothin
(6R,7R)-3-(acetylthiomethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate | 60% |
2-mercapto-5-methyl-1,3,4-thiadiazole
cephalothin
7β-(thiophen-2-acetamido)-3-<(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl>-ceph-3-em-4-carboxylic acid
Conditions | Yield |
---|---|
With phosphate buffer pH 6.4; sodium hydrogencarbonate at 60℃; for 5h; | 62% |
With phosphate buffer; sodium carbonate at 55 - 60℃; for 6h; |
3-methyl-5-mercapto-1,2,4-thiadiazole
cephalothin
Conditions | Yield |
---|---|
In ethyl acetate; 1,2-dichloro-ethane | 65% |
2-sulfanylpyrimidine
cephalothin
Conditions | Yield |
---|---|
With sodium acetate In acetic acid | 70.5% |
In acetonitrile |
Conditions | Yield |
---|---|
In ethanol; acetonitrile | 71% |
In ethanol; propiononitrile | 39% |
In ethanol; acetonitrile | |
In ethanol; 1,2-dichloro-ethane |
3-mercapto-4-methyl-5-oxo-6-hydroxy-4,5-dihydro-1,2,4-triazine
cephalothin
Conditions | Yield |
---|---|
In acetonitrile | 72.6% |
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