p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate

Base Information

• Chemical Name: p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate
• CAS No.: 108493-71-6
• Molecular Formula: C₂₄H₂₀F₃N₃O₁₀S
• Molecular Weight: 599.498
• Mol file: 108493-71-6.mol

Synonyms:p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate

Chemical Property of p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate

There total 11 articles about p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate 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: 95.0%

trifluoromethylsulfonic anhydride (358-23-6) + p-nitrobenzyl 7β-[(phenoxyacetyl)amino]-3-hydroxy-1-carba-1-dethia-3-cephem-4-carboxylate (119892-46-5) → p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate (108493-71-6)

Guidance literature:

With triethylamine; In dichloromethane; at -40 ℃; for 0.25h;

DOI:10.1021/jo971433w

Reference yield:

p-nitrobenzyl glyoxylate monohydrate (83654-96-0) → p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate (108493-71-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 4A molecular sieves / dimethylformamide; toluene / 8 h / Heating

2: pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 61 percent / SnCl₄ / CH₂Cl₂ / 6 h / 0 °C

4: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) -78 deg C to room temperature

5: 95 percent / Et₃N / CH₂Cl₂ / 0.25 h / -40 °C

With pyridine; dimethylsulfide; 4 A molecular sieve; tin(IV) chloride; ozone; triethylamine; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo971433w

Reference yield:

(3R-trans)-3-phenoxyacetylamino-4-phenylsulfonyl-2-azetidinone (88002-47-5) → p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate (108493-71-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 99 percent

2: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 30 min

3: 1.7 g / conc. HCl / tetrahydrofuran / 0.5 h / Ambient temperature

4: LiAl(t-BuO)3H / tetrahydrofuran / 0.75 h / 0 °C

5: 4A molecular sieves / dimethylformamide; toluene / 8 h / Heating

6: pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

7: 61 percent / SnCl₄ / CH₂Cl₂ / 6 h / 0 °C

8: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) -78 deg C to room temperature

9: 95 percent / Et₃N / CH₂Cl₂ / 0.25 h / -40 °C

With pyridine; hydrogenchloride; dimethylsulfide; 4 A molecular sieve; tin(IV) chloride; ozone; lithium tri-t-butoxyaluminum hydride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo971433w

upstream raw materials:

trifluoromethylsulfonic anhydride

p-nitrobenzyl 7β-[(phenoxyacetyl)amino]-3-hydroxy-1-carba-1-dethia-3-cephem-4-carboxylate

p-nitrobenzyl glyoxylate monohydrate

(3R-trans)-3-phenoxyacetylamino-4-phenylsulfonyl-2-azetidinone

Downstream raw materials:

(6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-1-aza-bicyclo[4.2.0]oct-2-ene-2,3-dicarboxylic acid 3-methyl ester 2-(4-nitro-benzyl) ester

(6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-1-aza-bicyclo[4.2.0]oct-2-ene-2,3-dicarboxylic acid 2-(4-nitro-benzyl) ester 3-propyl ester

p-nitrobenzyl (7S,6R)-7-(2-thienylacetamido)-3-<<(trifluoromethyl)sulfonyl>oxy>-1-carba-1-dethia-3-cephem-4-carboxylate

p-nitrobenzyl(6R,7S)-(phenoxyacetamido)-1-carba-1-dethia-3-carbethoxy-3-cephem-4-carboxylate