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
Hs Code.:

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

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

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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%

: 358-23-6
trifluoromethylsulfonic anhydride

: 119892-46-5
p-nitrobenzyl 7β-[(phenoxyacetyl)amino]-3-hydroxy-1-carba-1-dethia-3-cephem-4-carboxylate

: 108493-71-6
p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate

Guidance literature:: With triethylamine; In dichloromethane; at -40 ℃; for 0.25h;
DOI:10.1021/jo971433w

Reference yield:

: 83654-96-0
p-nitrobenzyl glyoxylate monohydrate

: 108493-71-6
p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate

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:

: 88002-47-5
(3R-trans)-3-phenoxyacetylamino-4-phenylsulfonyl-2-azetidinone

: 108493-71-6
p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate

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