(2S,5R,6S)-Benzhydryl 6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide

Base Information

• Chemical Name: (2S,5R,6S)-Benzhydryl 6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide
• CAS No.: 80353-26-0
• Molecular Formula: C21H20BrNO4S
• Molecular Weight: 462.364
• DSSTox Substance ID: DTXSID20441618
• Nikkaji Number: J779.351K
• Mol file: 80353-26-0.mol

Synonyms:80353-26-0;(2S,5R,6S)-Benzhydryl 6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide;Benzhydryl (2S,5R,6S)-6-bromo-3,3-dimethyl-4,7-dioxo-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;DTXSID20441618;AKOS016007047;BS-49672;CS-0153885;D94795;A864705;(6beta-Bromopenicillanic acid diphenylmethyl)4-oxide;(2S,5R,6S)-Benzhydryl6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate4-oxide

Chemical Property of (2S,5R,6S)-Benzhydryl 6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 629.066°C at 760 mmHg
• PKA: -6.06±0.70(Predicted)
• Flash Point: 334.247°C
• PSA: 82.89000
• Density: 1.582g/cm³
• LogP: 3.96410
• Storage Temp.: 2-8°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 461.02964
• Heavy Atom Count: 28
• Complexity: 639

Purity/Quality:

97% ^*data from raw suppliers

6-Bromo-3,3-dimethyl-7-oxo-4-oxide-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicAcidDiphenylmethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N2C(S1=O)C(C2=O)Br)C(=O)OC(C3=CC=CC=C3)C4=CC=CC=C4)C
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1=O)[C@H](C2=O)Br)C(=O)OC(C3=CC=CC=C3)C4=CC=CC=C4)C

Technology Process of (2S,5R,6S)-Benzhydryl 6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide

There total 8 articles about (2S,5R,6S)-Benzhydryl 6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide 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: 96.8%

diphenylmethyl 6α-bromopenicillanate (74189-25-6) → 6α-bromopenicillan-3α-carboxylic acid diphenylmethyl ester-1β-oxide (80353-26-0)

Guidance literature:

With peracetic acid; In dichloromethane; water; at 25 ℃; for 0.0166667h; Temperature; Flow reactor;

DOI:10.1021/acs.oprd.1c00127

Reference yield: 89.8%

6α-bromopenicillan-3α-carboxylic acid-1β-oxide (79703-02-9) + diazodiphenylmethane (908093-98-1) → 6α-bromopenicillan-3α-carboxylic acid diphenylmethyl ester-1β-oxide (80353-26-0)

Guidance literature:

In dichloromethane; acetone; at -2 - 2 ℃; for 2h; Time;

Reference yield:

6-Aminopenicillanic Acid (551-16-6) → 6α-bromopenicillan-3α-carboxylic acid diphenylmethyl ester-1β-oxide (80353-26-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: H₂SO₄; KBr / ethanol / 0 - 5 °C

1.2: 91 percent / aq. NaNO₂ / ethanol / 0 - 5 °C

2.1: dicyclocarbodiimide; 4-dimethylaminopyridine / CH₂Cl₂ / 25 °C

3.1: 45.3 g / aq. H₂O₂ / phenol / 25 °C

With dmap; sulfuric acid; dihydrogen peroxide; dicyclohexyl-carbodiimide; potassium bromide; In ethanol; dichloromethane; phenol;

DOI:10.1055/s-2004-837299

upstream raw materials:

benzophenone hydrazone

6α-Bromopenicillanic acid

6-aminopenicillanic acid

diphenylmethyl 6α-bromopenicillanate

Downstream raw materials:

benzhydryl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide

benzhydryl 6α-bromopenicillanate S,S-dioxide

diphenylmethyl (2S,3R,5R)-3-formyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

benzhydryl 2β-hydroxymethyl-1,1-dioxopenicillanate

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