(Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetic acid

Base Information

• Chemical Name: (Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetic acid
• CAS No.: 75028-24-9
• Molecular Formula: C6H8N4O3S
• Molecular Weight: 216.221
• Hs Code.: 2934999090
• European Community (EC) Number: 616-178-3
• Mol file: 75028-24-9.mol

Synonyms:75028-24-9;(Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)acetic acid;(Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetic acid;MFCD14583152;UFTDZEXQFNFPFR-UHFFFAOYSA-N;SY034844;FT-0687269;2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)-acetic acid;2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetic acid

Chemical Property of (Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetic acid

Chemical Property:

• Melting Point: 169-170o C
• Boiling Point: 430.5±28.0 °C(Predicted)
• PKA: 2.44±0.41(Predicted)
• PSA: 138.93000
• Density: 1.71
• LogP: 0.52670
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 216.03171130
• Heavy Atom Count: 14
• Complexity: 247

Purity/Quality:

99% ^*data from raw suppliers

(Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)aceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCON=C(C1=NSC(=N1)N)C(=O)O
• Uses: (Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)acetic Acid is an important intermediate for the preparation of Ceftaroline which possesses antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) and P. aeruginosa.

Technology Process of (Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetic acid

There total 7 articles about (Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

(Z)-N-(3-(2-acetamido-1-(ethoxyimino)-2-oxoethyl)-1,2,4-thiadiazol-5-yl)pivalamide (1618104-04-3) → 2-Ethoxyimino-2-(5-amino-1,2,4-thiadiazole-3-yl)-acetic acid (75028-24-9)

Guidance literature:

(Z)-N-(3-(2-acetamido-1-(ethoxyimino)-2-oxoethyl)-1,2,4-thiadiazol-5-yl)pivalamide; With sodium hydroxide; In water; at 80 ℃; for 18h;

With hydrogenchloride; In water; at 5 ℃; pH=3; Reagent/catalyst; Temperature;

DOI:10.2174/1570178611888140602160120

Reference yield: 81.1%

(Z)-2-(5-amino-1,2,4-thiadiazole-3-yl)-2-ethoxyiminoacetonitrile (113080-37-8) → 2-Ethoxyimino-2-(5-amino-1,2,4-thiadiazole-3-yl)-acetic acid (75028-24-9)

Guidance literature:

With dihydrogen peroxide; sodium hydroxide; In methanol; water; at 10 - 60 ℃; for 32h; Temperature;

Reference yield: 45.2%

2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino) acetonitrile (344302-24-5) → 2-Ethoxyimino-2-(5-amino-1,2,4-thiadiazole-3-yl)-acetic acid (75028-24-9)

Guidance literature:

With sodium hydroxide; In water; at 65 - 70 ℃;

DOI:10.1007/s11164-013-1109-0

upstream raw materials:

2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino) acetonitrile

2-cyano-2-ethoxyiminoacetamide

ethoxymethylenemalononitrile

(Z)-N-(3-(2-acetamido-1-(ethoxyimino)-2-oxoethyl)-1,2,4-thiadiazol-5-yl)pivalamide

Downstream raw materials:

benzhydryl 2-<(4S)-4-<2-(5-amino-1,2,4-thiadiazol-3-yl)-(Z)-2-(ethoxyimino)acetylamino>-3-oxo-2-isoxazolidinyl>-5-oxo-2-tetrahydrofurancarboxylate

p-methoxybenzyl (6R,7R)-7-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)acetamido]-3-chloromethyl-3-cephem-4-carboxylate

2-[[5-(dichlorophosphinyl)amino]-1,2,4-thiadiazole-3-yl]-2(Z)-ethoxyiminoacetyl chloride