4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, 1,3-dihydro-3-oxo-1-isobenzofuranyl ester, (2S-(2alpha,5alpha,6beta(S*)))-

Base Information

• Chemical Name: 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, 1,3-dihydro-3-oxo-1-isobenzofuranyl ester, (2S-(2alpha,5alpha,6beta(S*)))-
• CAS No.: 47747-56-8
• Molecular Formula: C24H23 N3 O6 S
• Molecular Weight: 481.529
• DSSTox Substance ID: DTXSID1048540
• ChEMBL ID: CHEMBL2365789
• Mol file: 47747-56-8.mol

Synonyms:SCHEMBL34337;CHEMBL2365789;DTXSID1048540;4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, 1,3-dihydro-3-oxo-1-isobenzofuranyl ester, (2S-(2alpha,5alpha,6beta(S*)))-;(3-oxo-1H-2-benzofuran-1-yl) (2S,5R,6R)-6-[(2-amino-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Chemical Property of 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, 1,3-dihydro-3-oxo-1-isobenzofuranyl ester, (2S-(2alpha,5alpha,6beta(S*)))-

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 770.9°Cat760mmHg
• Flash Point: 420°C
• PSA: 153.33000
• Density: 1.48g/cm³
• LogP: 2.67500
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 481.13075664
• Heavy Atom Count: 34
• Complexity: 875

Purity/Quality:

98%min ^*data from raw suppliers

TALAMPICILLIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)OC4C5=CC=CC=C5C(=O)O4)C
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)OC4C5=CC=CC=C5C(=O)O4)C
• Uses: Antibacterial.
• Therapeutic Function: Antibacterial

Technology Process of 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, 1,3-dihydro-3-oxo-1-isobenzofuranyl ester, (2S-(2alpha,5alpha,6beta(S*)))-

There total 8 articles about 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, 1,3-dihydro-3-oxo-1-isobenzofuranyl ester, (2S-(2alpha,5alpha,6beta(S*)))- 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:

3-Bromophthalide (6940-49-4) → talampicillin (47747-56-8)

Guidance literature:

Multi-step reaction with 2 steps

1: KHCO₃ / dimethylformamide / 5 h / Ambient temperature

2: (i) PhNMe₂, PCl₅, CH₂Cl₂, (ii) MeOH, (iii) /BRN= 5405183/, PhNMe₂

With potassium hydrogencarbonate; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.24.102

Reference yield:

6β-((R)-2-benzylideneamino-2-phenyl-acetylamino)-penicillanic acid (Ξ)-3-oxo-1,3-dihydro-isobenzofuran-1-yl ester (59225-72-8) → talampicillin (47747-56-8)

Guidance literature:

With hydrogenchloride; In acetonitrile; Ambient temperature;

DOI:10.1248/cpb.24.102

Reference yield:

Penicillin G potassium (113-98-4) → talampicillin (47747-56-8)

Guidance literature:

Multi-step reaction with 2 steps

1: KHCO₃ / dimethylformamide / 5 h / Ambient temperature

2: (i) PhNMe₂, PCl₅, CH₂Cl₂, (ii) MeOH, (iii) /BRN= 5405183/, PhNMe₂

With potassium hydrogencarbonate; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.24.102

upstream raw materials:

3-Bromophthalide

6β-[(R)-2-(2-methoxycarbonyl-1-methyl-vinylamino)-2-phenyl-acetylamino]-penicillanic acid; potassium salt

6β-((R)-2-benzylideneamino-2-phenyl-acetylamino)-penicillanic acid (Ξ)-3-oxo-1,3-dihydro-isobenzofuran-1-yl ester

d(-)-alpha-phenylglycine chloride hydrochloride

Refernces