MDL-19592 free base

Base Information

• Chemical Name: MDL-19592 free base
• CAS No.: 71685-95-5
• Molecular Formula: C₁₇H₁₇N₃O₆S
• Molecular Weight: 391.404
• UNII: VNG3VK6NV4
• Mol file: 71685-95-5.mol

Synonyms:VNG3VK6NV4;MDL-19592 free base;RMI-19592 free base;UNII-VNG3VK6NV4;71685-95-5;5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((amino-1,3-benzodioxol-5-ylacetyl)amino)-3-methyl-8-oxo-, (6R-(6alpha,7beta(R*)))-;5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-((AMINO-1,3-BENZODIOXOL-5-YLACETYL)AMINO)-3-METHYL-8-OXO-, (6R-(6.ALPHA.,7.BETA.(R*)))-

Chemical Property of MDL-19592 free base

Chemical Property:

• XLogP3: 0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 391.08380644
• Heavy Atom Count: 27
• Complexity: 713

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(N2C(C(C2=O)NC(=O)C(C3=CC4=C(C=C3)OCO4)N)SC1)C(=O)O
• Isomeric SMILES: CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC4=C(C=C3)OCO4)N)SC1)C(=O)O

Technology Process of MDL-19592 free base

There total 7 articles about MDL-19592 free base 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:

(6R,7R)-7-((R)-2-Benzo[1,3]dioxol-5-yl-2-tert-butoxycarbonylamino-acetylamino)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid → (6R,7R)-7-((R)-2-Amino-2-benzo[1,3]dioxol-5-yl-acetylamino)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (71685-95-5)

Guidance literature:

With hydrogenchloride; In nitromethane; at -60 - -5 ℃;

DOI:10.1021/jm00178a011

Reference yield:

3-deacetyloxy-7-aminocephalosporanic acid (22252-43-3,26395-99-3,70287-30-8,72059-35-9) → (6R,7R)-7-((R)-2-Amino-2-benzo[1,3]dioxol-5-yl-acetylamino)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (71685-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Et₃N, EtOCOCl, 2.) Et₃N / 1.) THF, from -30 deg C to -6 deg C, 2.) THF, H₂O, from -4 deg C to 14 deg C , 4 h

2: HCl / nitromethane / -60 - -5 °C

With hydrogenchloride; chloroformic acid ethyl ester; triethylamine; In nitromethane;

DOI:10.1021/jm00178a011

Reference yield:

piperonal (120-57-0,30024-74-9) → (6R,7R)-7-((R)-2-Amino-2-benzo[1,3]dioxol-5-yl-acetylamino)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (71685-95-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 74 percent / ethanol; H₂O / 2 h / Heating

2: 35 percent / Ba(OH)2*8H₂O / H₂O / 18 h / Heating

4: 94 percent / Et₃N / H₂O; dioxane / 30 h / Ambient temperature

5: 1.) Et₃N, EtOCOCl, 2.) Et₃N / 1.) THF, from -30 deg C to -6 deg C, 2.) THF, H₂O, from -4 deg C to 14 deg C , 4 h

6: HCl / nitromethane / -60 - -5 °C

With hydrogenchloride; barium dihydroxide; chloroformic acid ethyl ester; triethylamine; In 1,4-dioxane; nitromethane; ethanol; water;

DOI:10.1021/jm00178a011

upstream raw materials:

3-deacetyloxy-7-aminocephalosporanic acid

piperonal

amino-benzo[1,3]dioxol-5-yl acetic acid

5-<3,4-(methylenedioxy)phenyl>hydantoin

Refernces