7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid
A
7-amino-3-methylenecepham-4-carboxylic acid
B
7-aminodesacetoxycephalosporanic acid
Conditions | Yield |
---|---|
With N,N-Bis(trimethylsilyl)urea; ammonium chloride; zinc In N,N-dimethyl-formamide 1.) 25 deg C, 13 min, 2.) 5 deg C, 18 min, 3.) 5 deg C, 30 min; | A 66.5% B 3.0 % Chromat. |
(6R)-7t-(2-chloro-acetylamino)-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
7-aminodesacetoxycephalosporanic acid
Conditions | Yield |
---|---|
With sodium hydroxide; thiourea In water |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
7-aminodesacetoxycephalosporanic acid
(Z)-7-[(2-amino-4-thiazolyl-2-methoxyiminoacetylamino)]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With dmap; triethylamine In water; acetone at 20℃; for 3.5h; Time; | 98.5% |
7-aminodesacetoxycephalosporanic acid
1,1,1,3,3,3-hexamethyl-disilazane
Conditions | Yield |
---|---|
With methanol; 2,3-Dimethylaniline; sodium 2-ethylhexanoic acid In ethyl acetate; isopropyl alcohol refluxing hexamethyldisilazane and aminodeacetoxycephalosporanic acid (EtOAc, 1.5-2 h), cooling to 10-15°C, addn. of PhNMe2 and Fe-complex, refluxing (2 h, stirring), filtration, MeOH addn., filtration, addn.of Na-salt, room temp. (30 min); filtration, washing (EtOAc), drying (vac.); | 89% |
Conditions | Yield |
---|---|
In ethanol for 6h; Reflux; | 75% |
di-isopropyl ether
trityl chloride
7-aminodesacetoxycephalosporanic acid
(E)-3-octene
Conditions | Yield |
---|---|
With triethylamine In chloroform; ethyl acetate; N,N-dimethyl-formamide | 60% |
With triethylamine In chloroform; ethyl acetate; N,N-dimethyl-formamide | 60% |
7-aminodesacetoxycephalosporanic acid
Conditions | Yield |
---|---|
53.8% |
α-fluorophenylacetic acid chloride
7-aminodesacetoxycephalosporanic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetone at 3℃; for 2h; | 33.4% |
1,1’ bis(sulfonylchloride)ferrocene
7-aminodesacetoxycephalosporanic acid
1,1,1,3,3,3-hexamethyl-disilazane
Conditions | Yield |
---|---|
With 2,3-Dimethylaniline; sodium 2-ethylhexanoic acid In ethyl acetate; isopropyl alcohol refluxing hexamethyldisilazane and 7-aminodeacetoxycephalosporanic acid(EtOAc, 1-1.5 h), cooling to 10-15°C, addn. of PhNMe2 and Fe-complex, refluxing with stirring (2 h), filtration, addn. of hexanoate saltin i-PrOH; filtration, volume reduction (vac.), crystn. on petroleum ether addn. (room temp., 1h), filtration, washing (petroleum ether), drying (vac.); | 32.7% |
7-aminodesacetoxycephalosporanic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetone at 3℃; for 2h; | 30% |
7-aminodesacetoxycephalosporanic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetone at 3℃; for 2h; | 28% |
3,4-dichloro-α-fluorophenylacetic acid chloride
7-aminodesacetoxycephalosporanic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetone at 3℃; for 2h; | 16% |
N,O-bis-(trimethylsilyl)-acetamide
7-aminodesacetoxycephalosporanic acid
C14H26N2O3SSi2
Conditions | Yield |
---|---|
In dichloromethane Heating; |
(2-Amino-thiazol-4-yl)-[(Z)-ethoxyimino]-acetyl chloride; hydrochloride
7-aminodesacetoxycephalosporanic acid
1,1,1,3,3,3-hexamethyl-disilazane
7-<2-(amino-4-thiazolyl)-(Z)-2-ethoxyiminoacetamido>-deacetoxycephalosporanic acid
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydrogencarbonate; 2,3-Dimethylaniline 1)reflux 8 hrs., 2 hrs. r.t., 2)water pH 2.7; Yield given. Multistep reaction; |
(2-Amino-thiazol-4-yl)-[(Z)-isopropoxyimino]-acetyl chloride; hydrochloride
7-aminodesacetoxycephalosporanic acid
1,1,1,3,3,3-hexamethyl-disilazane
7-<2-(2-amino-4-thiazolyl)-(Z)-2-isopropoxyiminoacetamido>deacetoxycephalosporanic acid
Conditions | Yield |
---|---|
With hydrogenchloride; sulfuric acid; sodium hydrogencarbonate 1)reflux 8 hrs., 1 hr. r.t., 2)water pH 2.0; Yield given. Multistep reaction; |
(2-Amino-thiazol-4-yl)-[(Z)-cyclopentyloxyimino]-acetyl chloride; hydrochloride
7-aminodesacetoxycephalosporanic acid
1,1,1,3,3,3-hexamethyl-disilazane
7-<2-(2-amino-4-thiazolyl)-(Z)-2-cyclopentyloxyiminoacetamido>deacetoxycaphalosporanic acid
Conditions | Yield |
---|---|
With hydrogenchloride; sulfuric acid; sodium hydrogencarbonate 1)reflux 8 hrs., r.t. 1 hr., 2)water pH 2.0; Yield given. Multistep reaction; |
(2-Amino-thiazol-4-yl)-[(Z)-cyclohexyloxyimino]-acetyl chloride; hydrochloride
7-aminodesacetoxycephalosporanic acid
1,1,1,3,3,3-hexamethyl-disilazane
7-<2-(2-amino-4-thiazolyl)-(Z)-2-cyclohexyliminoacetamido>deacetoxycephalosporanic acid
Conditions | Yield |
---|---|
With hydrogenchloride; sulfuric acid; sodium hydrogencarbonate 1)reflux 8 hrs., r.t. 1 hr., 2)water pH 2.0; Yield given. Multistep reaction; |
7-aminodesacetoxycephalosporanic acid
1,1,1,3,3,3-hexamethyl-disilazane
trimethylsilyl 7-aminodeacetoxycephalosporanate
Conditions | Yield |
---|---|
sulfuric acid In benzene | |
In 1,2-dichloro-ethane for 5h; Heating; |
7-aminodesacetoxycephalosporanic acid
3-methyl-2-oxo-2,3-dihydro-benzooxazole-5-carbonyl chloride
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
7-aminodesacetoxycephalosporanic acid
3-Ethyl-2-oxo-2,3-dihydro-benzooxazole-5-carbonyl chloride
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
7-aminodesacetoxycephalosporanic acid
Conditions | Yield |
---|---|
With bromine In methanol; water at 20℃; number "n" of bromine molecules consumed by one molecule of the compound;the rate of bromine comsumption;; |
2-(2-amino-4-thiazolyl)-2-methoxyiminoacetyl chloride hydrochloride
7-aminodesacetoxycephalosporanic acid
1,1,1,3,3,3-hexamethyl-disilazane
7-[{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetyl}amino]-3-methyl-ceph-3-eme-4-carboxylic acid
Conditions | Yield |
---|---|
1)reflux 8 hrs., 1 hr. r.t., 2)water pH 3.5; Yield given. Multistep reaction; |
D-2-p-hydroxyphenylglycine methyl ester
7-aminodesacetoxycephalosporanic acid
cefadroxil
Conditions | Yield |
---|---|
immobilised Pen G acylase In water Enzymatic reaction; |
7-aminodesacetoxycephalosporanic acid
7-[(5-Bromo-furan-2-carbonyl)-amino]-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1,2-dichloro-ethane / 5 h / Heating 2: pyridine / 1,2-dichloro-ethane / 1.) -10 deg C, 2 h, 2.) room temp., 1 h 3: aq. NaOH View Scheme |
7-aminodesacetoxycephalosporanic acid
7-[2-(2-Isopropyl-5-methyl-cyclohexyloxy)-acetylamino]-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1,2-dichloro-ethane / 5 h / Heating 2: pyridine / 1,2-dichloro-ethane / 1.) -10 deg C, 2 h, 2.) room temp., 1 h 3: aq. NaOH View Scheme |
7-aminodesacetoxycephalosporanic acid
7-[2-(3,4-Dimethoxy-phenyl)-acetylamino]-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1,2-dichloro-ethane / 5 h / Heating 2: pyridine / 1,2-dichloro-ethane / 1.) -10 deg C, 2 h, 2.) room temp., 1 h 3: aq. NaOH View Scheme |
7-aminodesacetoxycephalosporanic acid
7-[(5-Benzyl-furan-2-carbonyl)-amino]-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1,2-dichloro-ethane / 5 h / Heating 2: pyridine / 1,2-dichloro-ethane / 1.) -10 deg C, 2 h, 2.) room temp., 1 h 3: aq. NaOH View Scheme |
7-aminodesacetoxycephalosporanic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1,2-dichloro-ethane / 5 h / Heating 2: pyridine / 1,2-dichloro-ethane / 1.) -10 deg C, 2 h, 2.) room temp., 1 h View Scheme |
7-aminodesacetoxycephalosporanic acid
7-[2-(4-Isopropoxy-3-methoxy-phenyl)-acetylamino]-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1,2-dichloro-ethane / 5 h / Heating 2: pyridine / 1,2-dichloro-ethane / 1.) -10 deg C, 2 h, 2.) room temp., 1 h 3: aq. NaOH View Scheme |
IUPAC Name: (6R,7R)-7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Systematic of 7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene- (CAS NO.26395-99-3): 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-amino-3-methyl-8-oxo- ; EINECS 247-654-5
CAS NO: 26395-99-3
Molecular Formula of 7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene- (CAS NO.26395-99-3): C8H10N2O3S
Molecular Weight: 214.2416
Molecular Structure:
H bond acceptors: 5
H bond donors: 3
Freely Rotating Bonds: 2
Polar Surface Area: 75.15 Å2
Index of Refraction: 1.697
Molar Refractivity: 51.69 cm3
Molar Volume: 134 cm3
Surface Tension: 81.7 dyne/cm
Density of 7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene- (CAS NO.26395-99-3): 1.59 g/cm3
Flash Point: 266.8 °C
Enthalpy of Vaporization: 86.44 kJ/mol
Boiling Point: 517.6 °C at 760 mmHg
Vapour Pressure: 4.18E-12 mmHg at 25°C
Hazard Codes: Xn
Risk Statements: 42/43
R42/43: May cause sensitization by inhalation and skin contact.
Safety Statements: 36
S36: Wear suitable protective clothing.
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