(6R,7R)-7-{[(2E)-2-(2-Amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(5-methyl-2H-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | CAS No. 82547-58-8

(6R,7R)-7-{[(2E)-2-(2-Amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(5-methyl-2H-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Basic Information

CAS Number

82547-58-8

Molecular Formula

C16H17N9O5S2

Molecular Weight

479.5 g/mol

AD

Basic Physical Properties

Melting Point

>175°C (dec.)

CC1=NN(N=N1)CC2=C(N3C(C(C3=O)NC(=O)C(=NOC)C4=CSC(=N4)N)SC2)C(=O)O

InChI

InChI=1S/C16H17N9O5S2/c1-6-20-23-24(21-6)3-7-4-31-14-10(13(27)25(14)11(7)15(28)29)19-12(26)9(22-30-2)8-5-32-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,26)(H,28,29)/b22-9+/t10-,14-/m1/s1

InChIKey

XSPUSVIQHBDITA-KXDGEKGBSA-N

LogP

-1.190479999999998

Topological Polar Surface Area

190.80999999999997 Ų

Hydrogen Bond Donor/Acceptor

4 / 14

Complexity

871

Synonyms & References

English

  • Cefteram (INN)
  • SCHEMBL1650688
  • 82547-58-8
  • CHEMBL2105953
  • CEFTERAM [JAN]
  • Cefterame
  • Ceftetrame
  • D07655
  • CHEBI:135776
  • Cefteram [INN]
  • Ro 19-5247
  • (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(5-methyl-2H-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • CEFTERAM [WHO-DD]
  • 74CQ4Q3N63
  • NS00011584
  • 3-[(5-methyl-2H-tetrazol-2-yl)methyl]-7beta-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3,4-didehydrocepham-4-carboxyic acid
  • Cefteramum
  • Cefteram
  • NCGC00183016-01
  • CFTM
  • (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(5-methyltetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • C-2540
  • (+)-(6R,7R)-7-(2-(2-Amino-4-thiazolyl)glyoxylamido)-3-((5-methyl-2H-tetrazol-2-yl)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7(sup 2)-(Z)-(O-methyloxime)
  • CS-0024817
  • CEFTERAM [MI]
  • delta 2-Cefteram
  • UNII-74CQ4Q3N63
  • HY-106084
  • ro19-5247
  • Cefteramum [Latin]
  • J-001229

MDL Number

MFCD00864913

FAQ

What are the physical and chemical properties of (6R,7R)-7-{[(2E)-2-(2-Amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(5-methyl-2H-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (CAS: 82547-58-8)?

This compound is a crystalline solid with a molecular weight of approximately 545.66 g/mol. It has low solubility in water but is soluble in organic solvents like DMSO. It is highly reactive, particularly in its amide and carboxylic acid functionalities, and it can undergo hydrolysis under basic conditions.

How is (6R,7R)-7-{[(2E)-2-(2-Amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(5-methyl-2H-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (CAS: 82547-58-8) typically synthesized?

This compound is typically synthesized via multi-step reactions involving coupling of a tetrazole with an amide. Common synthetic methods include using conditions such as HATU or EDC/HOBt as coupling agents, and DMAP for catalysis. The reaction yields are generally moderate to good, depending on the purity of starting materials and reaction conditions.

What industries use (6R,7R)-7-{[(2E)-2-(2-Amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(5-methyl-2H-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (CAS: 82547-58-8)?

This compound is primarily used in the pharmaceutical industry due to its unique chemical structure and potential as a drug candidate. It may also find applications in the development of certain sensors and as a reagent in chemical synthesis.

What precautions should be taken when handling (6R,7R)-7-{[(2E)-2-(2-Amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(5-methyl-2H-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (CAS: 82547-58-8)?

When handling this compound, wear appropriate personal protective equipment (PPE) such as gloves, safety goggles, and laboratory coat. Work in a well-ventilated fume hood to minimize exposure. Spills should be cleaned up using appropriate tools and materials. Always refer to the Safety Data Sheet (SDS) for detailed handling and disposal information.

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