(2S,3R,5R)-3-Chlorocarbonyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (2S,3R,5R)-3-Chlorocarbonyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester
• CAS No.: 1026477-53-1
• Molecular Formula: C₂₁H₁₈ClNO₆S
• Molecular Weight: 447.896

Synonyms:(2S,3R,5R)-3-Chlorocarbonyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Chemical Property of (2S,3R,5R)-3-Chlorocarbonyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,5R)-3-Chlorocarbonyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

There total 8 articles about (2S,3R,5R)-3-Chlorocarbonyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 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:

(2S,3R,5R)-3-Methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-benzhydryl ester (182750-66-9) → (2S,3R,5R)-3-Chlorocarbonyl-3-methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (1026477-53-1)

Guidance literature:

With oxalyl dichloride; In N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(96)00575-6

Reference yield:

6-Aminopenicillanic Acid (551-16-6) → (2S,3R,5R)-3-Chlorocarbonyl-3-methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (1026477-53-1)

Guidance literature:

Multi-step reaction with 10 steps

1: sulfuric acid; potassium bromide; sodium nitrite / ethanol / 3.5 h / 6 - 8 °C

2: peracetic acid; potassium iodide / dichloromethane; water / 1 h / 0 °C

3: acetic acid; zinc / acetonitrile / 1 h / 0 °C

4: toluene / 2 h / 114 °C

5: silver(I) acetate / dichloromethane / 4 h / 20 °C

6: potassium permanganate; acetic acid / water; acetone / 1 h / 20 °C

7: thiourea / ethanol / 1 h / 70 °C

8: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

9: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / tetrahydrofuran; tert-butyl alcohol / 1 h / 20 °C

10: pyridine; oxalyl dichloride / dichloromethane / 1 h / 20 °C

With pyridine; peracetic acid; sodium chlorite; potassium permanganate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; sulfuric acid; silver(I) acetate; Dess-Martin periodane; acetic acid; thiourea; potassium iodide; potassium bromide; zinc; sodium nitrite; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1128/AAC.06099-11

Reference yield:

benzhydryl 2β-hydroxymethyl-1,1-dioxopenicillanate (182750-65-8) → (2S,3R,5R)-3-Chlorocarbonyl-3-methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (1026477-53-1)

Guidance literature:

Multi-step reaction with 3 steps

1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

2: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / tetrahydrofuran; tert-butyl alcohol / 1 h / 20 °C

3: pyridine; oxalyl dichloride / dichloromethane / 1 h / 20 °C

With pyridine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;

DOI:10.1128/AAC.06099-11

upstream raw materials:

(2S,3R,5R)-3-Methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-benzhydryl ester

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

6-Aminopenicillanic Acid

benzhydryl 2β-hydroxymethyl-1,1-dioxopenicillanate

Downstream raw materials:

(2S,3R,5R)-3-(4-Benzyl-piperazine-1-carbonyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

(2S,3R,5R)-3-((S)-2-tert-Butoxycarbonyl-pyrrolidine-1-carbonyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

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