5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((5-methyl-1,3,4-thiadiazol-2-yl)thio)-8-oxo-7-((phenylacetyl)amino)-, (6R,7R)-

Base Information

Chemical Name:5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((5-methyl-1,3,4-thiadiazol-2-yl)thio)-8-oxo-7-((phenylacetyl)amino)-, (6R,7R)-
CAS No.:179034-83-4
Molecular Formula:C18H16N4O4S3
Molecular Weight:448.547
Hs Code.:
UNII:9031SV3FWE
Nikkaji Number:J1.195.396D
Wikidata:Q27271270
ChEMBL ID:CHEMBL105253
Mol file:179034-83-4.mol

Synonyms:FR 182024;FR-182024;FR182024

Suppliers and Price of 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((5-methyl-1,3,4-thiadiazol-2-yl)thio)-8-oxo-7-((phenylacetyl)amino)-, (6R,7R)-

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

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Total 2 raw suppliers

Chemical Property of 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((5-methyl-1,3,4-thiadiazol-2-yl)thio)-8-oxo-7-((phenylacetyl)amino)-, (6R,7R)-

Chemical Property:

XLogP3:1.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:6
Exact Mass:448.03336853
Heavy Atom Count:29
Complexity:728

Purity/Quality:: 99.90% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC1=NN=C(S1)SC2=C(N3C(C(C3=O)NC(=O)CC4=CC=CC=C4)SC2)C(=O)O
Isomeric SMILES:CC1=NN=C(S1)SC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)CC4=CC=CC=C4)SC2)C(=O)O

Technology Process of 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((5-methyl-1,3,4-thiadiazol-2-yl)thio)-8-oxo-7-((phenylacetyl)amino)-, (6R,7R)-

There total 3 articles about 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((5-methyl-1,3,4-thiadiazol-2-yl)thio)-8-oxo-7-((phenylacetyl)amino)-, (6R,7R)- 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: 64.0%

: 179034-64-1
benzhydryl 7β-(2-phenylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate

: 179034-83-4
(6R,7R)-3-(5-Methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Guidance literature:: With methoxybenzene; trifluoroacetic acid; In dichloromethane;
DOI:10.1016/S0960-894X(99)00549-1

Reference yield:

: 54639-48-4
(6R,7R)-benzhydryl 3-hydroxy-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

: 179034-83-4
(6R,7R)-3-(5-Methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: 92 percent / K₂CO₃ / dimethylformamide / 1 h / -20 °C

2.1: tBuOK / tetrahydrofuran; 1,2-dimethoxy-ethane / 0.33 h / -10 °C

2.2: 58 percent / tetrahydrofuran; 1,2-dimethoxy-ethane / 2 h / -10 - 5 °C

3.1: 58 percent / TFA / CH₂Cl₂; methoxybenzene / 1 h / 0 °C

With potassium tert-butylate; potassium carbonate; trifluoroacetic acid; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; methoxybenzene; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: deprotonation / 2.2: Substitution / 3.1: Substitution;
DOI:10.1016/S0968-0896(00)00163-2

Reference yield:

: 92096-37-2
benzhydryl (6R,7R)-7β-[(phenylacetyl)amino]-3-[(methylsulfonyl)oxy]-3-cephem-4-carboxylate

: 179034-83-4
(6R,7R)-3-(5-Methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: tBuOK / tetrahydrofuran; 1,2-dimethoxy-ethane / 0.33 h / -10 °C

1.2: 58 percent / tetrahydrofuran; 1,2-dimethoxy-ethane / 2 h / -10 - 5 °C

2.1: 58 percent / TFA / CH₂Cl₂; methoxybenzene / 1 h / 0 °C

With potassium tert-butylate; trifluoroacetic acid; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; methoxybenzene; 1.1: deprotonation / 1.2: Substitution / 2.1: Substitution;
DOI:10.1016/S0968-0896(00)00163-2