(7R)-7-[(phenylacetyl)amino]-3-[2,4-bis(chloromethyl)phenylthio]-3-cephem-4-carboxylate, 4-methoxybenzyl ester

Base Information

Chemical Name:(7R)-7-[(phenylacetyl)amino]-3-[2,4-bis(chloromethyl)phenylthio]-3-cephem-4-carboxylate, 4-methoxybenzyl ester
CAS No.:214341-20-5
Molecular Formula:C₃₁H₂₈Cl₂N₂O₅S₂
Molecular Weight:643.612
Hs Code.:

Synonyms:(7R)-7-[(phenylacetyl)amino]-3-[2,4-bis(chloromethyl)phenylthio]-3-cephem-4-carboxylate, 4-methoxybenzyl ester

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Chemical Property of (7R)-7-[(phenylacetyl)amino]-3-[2,4-bis(chloromethyl)phenylthio]-3-cephem-4-carboxylate, 4-methoxybenzyl ester

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Technology Process of (7R)-7-[(phenylacetyl)amino]-3-[2,4-bis(chloromethyl)phenylthio]-3-cephem-4-carboxylate, 4-methoxybenzyl ester

There total 8 articles about (7R)-7-[(phenylacetyl)amino]-3-[2,4-bis(chloromethyl)phenylthio]-3-cephem-4-carboxylate, 4-methoxybenzyl 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: 87.0%

: 214341-19-2
(7R)-7-[(phenylacetyl)amino]-3-[2,4-bis(hydroxymethyl)phenylthio]-3-cephem-4-carboxylate, 4-methoxybenzyl ester

: 214341-20-5
(7R)-7-[(phenylacetyl)amino]-3-[2,4-bis(chloromethyl)phenylthio]-3-cephem-4-carboxylate, 4-methoxybenzyl ester

Guidance literature:: With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; lithium chloride; In N,N-dimethyl-formamide;
DOI:10.7164/antibiotics.51.722

Reference yield:

: 5985-24-0
dimethyl 4-hydroxyisophthalate

: 214341-20-5
(7R)-7-[(phenylacetyl)amino]-3-[2,4-bis(chloromethyl)phenylthio]-3-cephem-4-carboxylate, 4-methoxybenzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 74 percent / triethylamine / dimethylformamide / 6 h / 20 °C

2: 97 percent / xylene / 5 h / 170 °C

3: 91 percent / potassium hydroxide / ethanol / 4 h / Heating

4: 100 percent / BH₃ / tetrahydrofuran

5: 61 percent / sodium methoxide / methanol / 1 h / 20 °C

6: 59 percent / dimethylformamide / 1 h / -40 °C

7: 87 percent / lithium chloride; diisopropylethylamine; methanesulfonyl chliride / dimethylformamide

With potassium hydroxide; borane; sodium methylate; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; xylene; 1: Substitution / 2: Isomerization / 3: Hydrolysis / 4: Reduction / 5: Substitution / 6: Substitution / 7: Substitution;
DOI:10.7164/antibiotics.51.722

Reference yield:

: 123054-30-8
(7R)-7-[(phenylacetyl)amino]-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate, 4-methoxybenzyl ester

: 214341-20-5
(7R)-7-[(phenylacetyl)amino]-3-[2,4-bis(chloromethyl)phenylthio]-3-cephem-4-carboxylate, 4-methoxybenzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 59 percent / dimethylformamide / 1 h / -40 °C

2: 87 percent / lithium chloride; diisopropylethylamine; methanesulfonyl chliride / dimethylformamide

With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; lithium chloride; In N,N-dimethyl-formamide; 1: Substitution / 2: Substitution;
DOI:10.7164/antibiotics.51.722