26395-99-3

Basic information

• Product Name: 7-Aminodesacetoxycephalosporanic acid
• Synonyms: 7-Amino-3-methyl-3-cephem-4-carboxylic acid(7-ADCA);( 7-AMINO DESACETOXY CEPALOSPHORANIC ACID;7-AMINODESACETOXYCEPHALOSPORANIC ACID, 98;7-Phenglacetamido-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester;7-ADCA 98.5+%;7-ADCA;7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;7-Aminodesacetoxycephalosporanic acid
• CAS NO: 26395-99-3
• Molecular Formula: C₈H₁₀N₂O₃S
• Molecular Weight: 214.24
• EINECS: 247-654-5
• Product Categories: pharmacetical
• Mol File: 26395-99-3.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 517.598 °C at 760 mmHg
• Flash Point: 266.834 °C
• Appearance: /
• Density: 1.598 g/cm³
• Vapor Pressure: 4.18E-12mmHg at 25°C
• Refractive Index: 1.697
• Storage Temp.: -20°C Freezer
• Solubility: Aqueous Base (Slightly), DMSO (Very Slightly, Heated)
• PKA: 3.04±0.50(Predicted)
• CAS DataBase Reference: 7-Aminodesacetoxycephalosporanic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Aminodesacetoxycephalosporanic acid(26395-99-3)
• EPA Substance Registry System: 7-Aminodesacetoxycephalosporanic acid(26395-99-3)

Safety Data

• Hazard Codes: Xn
• Statements: 42/43
• Safety Statements: 36
• Hazardous Substances Data: 26395-99-3(Hazardous Substances Data)

Usage

Uses

7-Aminodesacetoxycephalosporanic Acid (Cefadroxil EP Impurity B) is a metabolite of Cephalexin (C256800).

InChI:InChI=1/C8H10N2O3S/c1-3-2-14-7-4(9)6(11)10(7)5(3)8(12)13/h4,7H,2,9H2,1H3,(H,12,13)/t4-,7-/m0/s1

Synthetic route

7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid (30246-33-4) → 7-amino-3-methylenecepham-4-carboxylic acid (36996-01-7, 51795-31-4) + 7-aminodesacetoxycephalosporanic acid (26395-99-3)

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 (40818-86-8) → 7-aminodesacetoxycephalosporanic acid (26395-99-3)

Conditions	Yield
With sodium hydroxide; thiourea In water

(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate (80756-85-0) + 7-aminodesacetoxycephalosporanic acid (26395-99-3) → (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 (65052-63-3, 65052-69-9)

Conditions	Yield
With dmap; triethylamine In water; acetone at 20℃; for 3.5h; Time;	98.5%

ferrocene sulfonyl chloride + 7-aminodesacetoxycephalosporanic acid (26395-99-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → sodium ferrocenylsulphoamidodeacetoxycephalosporanate

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%

4-bromo-benzaldehyde (1122-91-4) + 7-aminodesacetoxycephalosporanic acid (26395-99-3) → C15H13BrN2O3S

Conditions	Yield
In ethanol for 6h; Reflux;	75%

2-carboxy-3-methyl-8-oxo-7-tritylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene + di-isopropyl ether (108-20-3) + trityl chloride (76-83-5) + 7-aminodesacetoxycephalosporanic acid (26395-99-3) → (E)-3-octene (14919-01-8)

Conditions	Yield
With triethylamine In chloroform; ethyl acetate; N,N-dimethyl-formamide	60%
With triethylamine In chloroform; ethyl acetate; N,N-dimethyl-formamide	60%

(-)-α-(tert-Butyloxycarbonylamino)-4-hydroxy-3-[(methylthio)methyl]benzeneacetic acid + 7-aminodesacetoxycephalosporanic acid (26395-99-3) → 7-[[(tert-Butyloxycarbonylamino)-[4-hydroxy-3-[(methylthio)methyl]phenyl]acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions	Yield
	53.8%

α-fluorophenylacetic acid chloride (22692-94-0) + 7-aminodesacetoxycephalosporanic acid (26395-99-3) → 7-<(α-fluorophenylacetyl)amino>-3-methyl-3-cephem-4-carboxylic acid

Conditions	Yield
With sodium hydrogencarbonate In water; acetone at 3℃; for 2h;	33.4%

1,1’ bis(sulfonylchloride)ferrocene (41686-87-7) + 7-aminodesacetoxycephalosporanic acid (26395-99-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → sodium 1,1'-ferrocenylendisulphonamido-deacetoxycephalosporanate

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 (26395-99-3) + 2-dibenzofuranacetic acid chloride → 7-(<2-(dibenzofuran-2-yl)acetyl>amino)-3-methyl-3-cephem-4-carboxylic acid

Conditions	Yield
With sodium hydrogencarbonate In water; acetone at 3℃; for 2h;	30%

7-aminodesacetoxycephalosporanic acid (26395-99-3) + Dibenzofuran-2-yl-fluoro-acetyl chloride → 7-(2-Dibenzofuran-2-yl-2-fluoro-acetylamino)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions	Yield
With sodium hydrogencarbonate In water; acetone at 3℃; for 2h;	28%

3,4-dichloro-α-fluorophenylacetic acid chloride (53938-46-8) + 7-aminodesacetoxycephalosporanic acid (26395-99-3) → 7-<(3,4-dichloro-α-fluorophenylacetyl)amino>-3-methyl-3-cephem-4-carboxylic acid

Conditions	Yield
With sodium hydrogencarbonate In water; acetone at 3℃; for 2h;	16%

N,O-bis-(trimethylsilyl)-acetamide (10416-59-8) + 7-aminodesacetoxycephalosporanic acid (26395-99-3) → C14H26N2O3SSi2 (31461-05-9)

Conditions	Yield
In dichloromethane Heating;

(2-Amino-thiazol-4-yl)-[(Z)-ethoxyimino]-acetyl chloride; hydrochloride (124219-60-9) + 7-aminodesacetoxycephalosporanic acid (26395-99-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 7-<2-(amino-4-thiazolyl)-(Z)-2-ethoxyiminoacetamido>-deacetoxycephalosporanic acid (124827-23-2)

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 (123657-22-7) + 7-aminodesacetoxycephalosporanic acid (26395-99-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 7-<2-(2-amino-4-thiazolyl)-(Z)-2-isopropoxyiminoacetamido>deacetoxycephalosporanic acid (123657-23-8)

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 (124219-61-0) + 7-aminodesacetoxycephalosporanic acid (26395-99-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 7-<2-(2-amino-4-thiazolyl)-(Z)-2-cyclopentyloxyiminoacetamido>deacetoxycaphalosporanic acid (123657-25-0)

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 (123657-20-5) + 7-aminodesacetoxycephalosporanic acid (26395-99-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 7-<2-(2-amino-4-thiazolyl)-(Z)-2-cyclohexyliminoacetamido>deacetoxycephalosporanic acid (123657-21-6)

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 (26395-99-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → trimethylsilyl 7-aminodeacetoxycephalosporanate (41360-37-6)

Conditions	Yield
sulfuric acid In benzene
In 1,2-dichloro-ethane for 5h; Heating;

7-aminodesacetoxycephalosporanic acid (26395-99-3) + 3-methyl-2-oxo-2,3-dihydro-benzooxazole-5-carbonyl chloride (154780-55-9) → 3-Methyl-7-[(3-methyl-2-oxo-2,3-dihydro-benzooxazole-5-carbonyl)-amino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions	Yield
Yield given. Multistep reaction;

7-aminodesacetoxycephalosporanic acid (26395-99-3) + 3-Ethyl-2-oxo-2,3-dihydro-benzooxazole-5-carbonyl chloride (154780-56-0) → 7-[(3-Ethyl-2-oxo-2,3-dihydro-benzooxazole-5-carbonyl)-amino]-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions	Yield
Yield given. Multistep reaction;

7-aminodesacetoxycephalosporanic acid (26395-99-3) → decomposition products are similar to the products of decomposition of cefotaxime;

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 (116585-13-8) + 7-aminodesacetoxycephalosporanic acid (26395-99-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) + sulfuric acid, dimethylaniline, → 7-[{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetyl}amino]-3-methyl-ceph-3-eme-4-carboxylic acid (65052-63-3, 65052-69-9)

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 (37763-23-8) + 7-aminodesacetoxycephalosporanic acid (26395-99-3) → cefadroxil (50370-12-2)

Conditions	Yield
immobilised Pen G acylase In water Enzymatic reaction;

7-aminodesacetoxycephalosporanic acid (26395-99-3) → 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 (102907-73-3)

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 (26395-99-3) → 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 (102907-77-7)

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 (26395-99-3) → 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 (102907-68-6)

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 (26395-99-3) → 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 (102907-74-4)

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 (26395-99-3) → C16H19BrN2O5SSi

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 (26395-99-3) → 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 (102907-70-0)

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

Upstream product

• 40818-86-8 (6R)-7t-(2-chloro-acetylamino)-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 54011-14-2 acetoxymethyl 7β-phenylacetamido-3-methyl-3-cephem-4-carboxylate 
• 60779-48-8 acetoxymethyl 7-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate 
• 27255-72-7 7-phenylacetamidodesacetoxycephalosporanic acid 
• 60758-77-2 7β-(4-Carboxybutanamido)desacetoxycephalosporanic acid 
• 983-85-7 Maripen 
• 81244-83-9 acetoxymethyl 6-(phenoxyacetamido)-penicillanate 1-oxide 
• 75-78-5 dimethylsilicon dichloride 
• 101-83-7 N-cyclohexyl-cyclohexanamine 
• 30246-33-4 7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid 
• 101-02-0 triphenyl phosphite 
• 75-36-5 acetyl chloride 
• 87-69-4 tartaric acid 
• 855904-39-1 N-ethyl-N-hexadecylaniline 

Downstream Products

• 36954-81-1 (6R)-7t-benzylideneamino-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester 
• 73387-42-5 (6R)-3-acetoxymethyl-7t-(2-nitro-benzene(Ξ)sulfinylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 95107-17-8 trimethylsilyl (6R,7R)-7-(4-nitrobenzylidene)amino-3-methylceph-3-em-4-carboxylate 
• 37850-81-0 7β-salicylideneamino-3-methyl-3-cephem-4-carboxylic acid 
• 122348-09-8 N-Salicylidene-7-amino-3-desacetoxycephalosporanic acid tert-butylamine salt 
• 144790-28-3 L-cefadroxil 
• 611-71-2 (R)-Mandelic Acid 
• 52312-06-8 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 21732-17-2 1H-tetrazol-1-ylacetic acid 

Relevant articles and documents

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