benzhydryl 2-[2-(benzothiazol-2-yldisulfanyl)-3,3-dibromo-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoate

Base Information

• Chemical Name: benzhydryl 2-[2-(benzothiazol-2-yldisulfanyl)-3,3-dibromo-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoate
• CAS No.: 113823-60-2
• Molecular Formula: C₂₈H₂₂Br₂N₂O₃S₃
• Molecular Weight: 690.5

Synonyms:benzhydryl 2-[2-(benzothiazol-2-yldisulfanyl)-3,3-dibromo-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoate

Chemical Property of benzhydryl 2-[2-(benzothiazol-2-yldisulfanyl)-3,3-dibromo-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoate

Chemical Property:

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Technology Process of benzhydryl 2-[2-(benzothiazol-2-yldisulfanyl)-3,3-dibromo-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoate

There total 2 articles about benzhydryl 2-[2-(benzothiazol-2-yldisulfanyl)-3,3-dibromo-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoate 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: 84.0%

2-Mercaptobenzothiazole (149-30-4,118090-09-8) + diphenylmethyl (4R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 4-oxide (123285-25-6) → benzhydryl 2-[2-(benzothiazol-2-yldisulfanyl)-3,3-dibromo-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoate (113823-60-2)

Guidance literature:

In toluene; for 1h; Heating;

DOI:10.1021/ja063715w

Reference yield: 75.0%

benzhydryl 6,6-dibromopenicillanate 1-oxide (100298-37-1,113891-01-3,123285-25-6) + 2-Mercaptobenzothiazole (149-30-4,118090-09-8) → benzhydryl 2-[2-(benzothiazol-2-yldisulfanyl)-3,3-dibromo-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoate (113823-60-2)

Guidance literature:

In toluene; for 1h; Heating;

Reference yield: 90.0%

benzhydryl 2-[2-(benzothiazol-2-yldisulfanyl)-3,3-dibromo-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoate (113823-60-2) → benzhydryl 2β-chloromethyl-6,6-dibromopenicillanate (113823-59-9)

Guidance literature:

With sulfuryl dichloride; In dichloromethane; at -30 ℃; for 0.333333h;

upstream raw materials:

benzhydryl 6,6-dibromopenicillanate 1-oxide

2-Mercaptobenzothiazole

diphenylmethyl (4R)-6,6-dibromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 4-oxide

Downstream raw materials:

benzhydryl 2β-chloromethyl-6,6-dibromopenicillanate

(2S,5R)-3,3-Bis-chloromethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

(2S,3S,5R)-3-Bromomethyl-3-chloromethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

benzhydryl 2β-chloromethyl-6,6-dihydropenicillanate 1α-oxide

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