5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-amino-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-, (6R,7R)- supplier

Name
7-AMINO-3-[(5-METHYL-1,3,4-THIADIAZOL-2-YL)THIOMETHYL]CEPHALOSPHORANIC ACID
EINECS 250-099-1
CAS No. 30246-33-4
Article Data52
CAS DataBase
Density 1.72 g/cm³
Solubility
Melting Point
Formula C₁₁H₁₂N₄O₃S₃
Boiling Point 678.2 °C at 760 mmHg
Molecular Weight 344.439
Flash Point 364 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-amino-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo- (8CI);5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-amino-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-, (6R-trans)-;(6R-trans)-7-Amino-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid;7-Amino-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-d-3-cephem-4-carboxylic acid;7-Amino-3-[(2-methyl-1,3,4-thiadiazol-5-ylthio)methyl]-3-cephem-4-carboxylicacid;7-Amino-3-[(5-methyl-1,3,4-thiadiazol-2-ylthio)methyl]-3-cephem-4-carboxylicacid;
PSA 188.25000
LogP 1.15790

Synthetic route

: 29490-19-5
2-mercapto-5-methyl-1,3,4-thiadiazole

: 3-acetoxymethyl-7-aminoceph-3-em-4-carboxylic acid

: 30246-33-4
7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid

Conditions

Conditions	Yield
With boric acid; triethylamine In water	96%
In water; acetone
In water; acetone

: 3855-09-2
3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0 ]oct-2-ene-2-carboxylic acid sodium salt

: 29490-19-5
2-mercapto-5-methyl-1,3,4-thiadiazole

: 30246-33-4
7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water
With sodium hydrogencarbonate In water
With sodium hydrogencarbonate In water
With sodium hydrogencarbonate In water

: 123-75-1
pyrrolidine

: 30246-33-4
7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid

: 7-amino-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-2-(pyrrolidine-1-carbonyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one

Conditions

Conditions	Yield
With aluminum oxide at 120℃; for 0.0333333h; microwave irradiation;	93%

: 68787-52-0
2-amino-5-(3-pyridyl)-1,3,4-thiadiazole

: 30246-33-4
7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid

: 7-amino-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (5-pyridin-3-yl-[1,3,4]thiadiazol-2-yl)-amide

Conditions

Conditions	Yield
With aluminum oxide at 120℃; for 0.0166667h; microwave irradiation;	92%

: 100539-95-5
2-amino-5-undecyl-1,3,4-thiadiazole

: 30246-33-4
7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid

: 7-amino-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (5-undecyl-[1,3,4]thiadiazol-2-yl)-amide

Conditions

Conditions	Yield
With aluminum oxide at 120℃; for 0.0333333h; microwave irradiation;	90%

: 110-89-4
piperidine

: 30246-33-4
7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid

: 7-amino-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-2-(piperidine-1-carbonyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one

Conditions

Conditions	Yield
With aluminum oxide at 120℃; for 0.025h; microwave irradiation;	89%

: 2002-03-1
2-amino-5-phenyl-1,3,4-thiadiazole

: 30246-33-4
7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid

: 7-amino-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (5-phenyl-[1,3,4]thiadiazol-2-yl)-amide

Conditions

Conditions	Yield
With aluminum oxide at 120℃; for 0.0166667h; microwave irradiation;	87%

: 30246-33-4
7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid

: 28004-62-8
2-amino-5-(4-chlorophenyl)-1,3,4-thiadiazole

: 7-amino-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid [5-(4-chloro-phenyl)-[1,3,4]thiadiazol-2-yl]-amide

Conditions

Conditions	Yield
With aluminum oxide at 120℃; for 0.025h; microwave irradiation;	86%

: 108-33-8
5-methyl-1,3,4-thiadiazol-2-amine

: 30246-33-4
7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid

: 7-amino-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (5-methyl-[1,3,4]thiadiazol-2-yl)-amide

Conditions

Conditions	Yield
With aluminum oxide at 120℃; for 0.025h; microwave irradiation;	85%

: 30246-33-4
7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid

: 113836-51-4
5-nonyl-[1,3,4]thiadiazol-2-ylamine

: 7-amino-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (5-nonyl-[1,3,4]thiadiazol-2-yl)-amide

Conditions

Conditions	Yield
With aluminum oxide at 120℃; for 0.025h; microwave irradiation;	83%

: 30246-33-4
7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid

A: 36996-01-7, 51795-31-4
7-amino-3-methylenecepham-4-carboxylic acid

B: 26395-99-3
7-aminodesacetoxycephalosporanic acid

Conditions

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.

: 30246-33-4
7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid

: 68403-70-3, 115889-60-6
7-amino-3-hydroxycepham-4-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 66.5 percent / bis(trimethylsilyl)urea (BSU), NH4Cl, zinc dust / dimethylformamide / 1.) 25 deg C, 13 min, 2.) 5 deg C, 18 min, 3.) 5 deg C, 30 min 2: 1.) MsOH, ozone, 2.) NaBH4, NaOH / 1.) MeOH, -75 deg C, 2.) MeOH/H2O, 0 - 10 deg C View Scheme

: 30246-33-4
7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid

: 115824-01-6, 121055-15-0
3-methylene-7-phenylacetamidocepham-4-carboxylic acid 1-sulfoxide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 66.5 percent / bis(trimethylsilyl)urea (BSU), NH4Cl, zinc dust / dimethylformamide / 1.) 25 deg C, 13 min, 2.) 5 deg C, 18 min, 3.) 5 deg C, 30 min 2: 1.) ozone, MsOH, 2.) NaBH4 / 1.) MeOH, -40 deg C, 2.) MeOH/H2O, 3.) pH 6.5 - 7.5 View Scheme

: 30246-33-4
7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid

: 90305-32-1, 115889-59-3
3-hydroxy-7-phenylacetamido-cepham-4-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 66.5 percent / bis(trimethylsilyl)urea (BSU), NH4Cl, zinc dust / dimethylformamide / 1.) 25 deg C, 13 min, 2.) 5 deg C, 18 min, 3.) 5 deg C, 30 min 2: 1.) ozone, MsOH, 2.) NaBH4 / 1.) MeOH, -40 deg C, 2.) MeOH/H2O, 3.) pH 6.5 - 7.5 View Scheme

: 30246-33-4
7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid

: 7-[[2-carboethoxy-2-(1-pyrryl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

: 108260-00-0
7-aminocephalosporanic acid

: 30246-33-4
7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid

: 115-11-7
isobutene

: 6187-87-7, 102253-55-4
3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With sulfuric acid; sodium hydrogencarbonate In 1,4-dioxane; ethyl acetate; 7-aminodesacetoxycephalosporanic acid

...Expand

: 30246-33-4
7-amino-3-(5'-methyl-1',3',4'-thiadiazol-2'-ylthiomethyl)cephalosporanic acid

A: 54895-35-1
7-amino-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid t-butyl ester

B: 6187-87-7, 102253-55-4
3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
In 7-aminodesacetoxycephalosporanic acid

5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-amino-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-, (6R,7R)- Specification

The 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-amino-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-, (6R,7R)-, with the CAS registry number 30246-33-4, is also known as (6R-trans)-7-Amino-3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid. Its EINECS registry number is 250-099-1. This chemical's molecular formula is C₁₁H₁₂N₄O₃S₃ and molecular weight is 344.43. Its IUPAC name is called (7R)-7-amino-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.

Physical properties of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-amino-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-, (6R,7R)-: (1)ACD/LogP: 0.42; (2)ACD/LogD (pH 5.5): -2.32; (3)ACD/LogD (pH 7.4): -3.28; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 7; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 5; (11)Index of Refraction: 1.768; (12)Molar Refractivity: 82.78 cm³; (13)Molar Volume: 199.4 cm³; (14)Surface Tension: 108.5 dyne/cm; (15)Density: 1.72 g/cm³; (16)Flash Point: 364 °C; (17)Enthalpy of Vaporization: 104.57 kJ/mol; (18)Boiling Point: 678.2 °C at 760 mmHg; (19)Vapour Pressure: 2.53E-19 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC1=NN=C(S1)SCC2=C(N3C(C(C3=O)N)SC2)C(=O)O
(2)Isomeric SMILES: CC1=NN=C(S1)SCC2=C(N3C([C@@H](C3=O)N)SC2)C(=O)O
(3)InChI: InChI=1S/C11H12N4O3S3/c1-4-13-14-11(21-4)20-3-5-2-19-9-6(12)8(16)15(9)7(5)10(17)18/h6,9H,2-3,12H2,1H3,(H,17,18)/t6-,9?/m1/s1
(4)InChIKey: HJSGHKMSDOLGJJ-VJSCVCEBSA-N

Product Name

7-AMINO-3-[(5-METHYL-1,3,4-THIADIAZOL-2-YL)THIOMETHYL]CEPHALOSPHORANIC ACID

Synthetic route

5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-amino-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-, (6R,7R)- Specification

Related Products

Hot Products