methyl (2S,3R,4R)-1-benzoyl-4-(4-bromophenylthio)-3-(tert-butoxycarbonylmethyl)pyrrolidine-2-carboxylate

Base Information

• Chemical Name: methyl (2S,3R,4R)-1-benzoyl-4-(4-bromophenylthio)-3-(tert-butoxycarbonylmethyl)pyrrolidine-2-carboxylate
• CAS No.: 960009-08-9
• Molecular Formula: C₂₅H₂₈BrNO₅S
• Molecular Weight: 534.471

Synonyms:methyl (2S,3R,4R)-1-benzoyl-4-(4-bromophenylthio)-3-(tert-butoxycarbonylmethyl)pyrrolidine-2-carboxylate

Chemical Property of methyl (2S,3R,4R)-1-benzoyl-4-(4-bromophenylthio)-3-(tert-butoxycarbonylmethyl)pyrrolidine-2-carboxylate

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Technology Process of methyl (2S,3R,4R)-1-benzoyl-4-(4-bromophenylthio)-3-(tert-butoxycarbonylmethyl)pyrrolidine-2-carboxylate

There total 2 articles about methyl (2S,3R,4R)-1-benzoyl-4-(4-bromophenylthio)-3-(tert-butoxycarbonylmethyl)pyrrolidine-2-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: 96.0%

bis(4-bromophenyl)disulfide (5335-84-2) + (2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester (303188-61-6) → methyl (2S,3R,4R)-1-benzoyl-4-(4-bromophenylthio)-3-(tert-butoxycarbonylmethyl)pyrrolidine-2-carboxylate (960009-08-9)

Guidance literature:

With tributylphosphine; In toluene; at 90 ℃; for 3.75h; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.02.018

Reference yield: 48.0%

para-bromobenzenethiol (106-53-6) + (2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester (303188-61-6) → methyl (2S,3R,4R)-1-benzoyl-4-(4-bromophenylthio)-3-(tert-butoxycarbonylmethyl)pyrrolidine-2-carboxylate (960009-08-9)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 0.5h;

Reference yield: 89.0%

methyl (2S,3R,4R)-1-benzoyl-4-(4-bromophenylthio)-3-(tert-butoxycarbonylmethyl)pyrrolidine-2-carboxylate (960009-08-9) → (2S,3R,4R)-3-carboxy-methyl-4-(4-bromophenylthio)-pyrrolidine-2-carboxylic acid (960009-07-8)

Guidance literature:

With hydrogenchloride; water; at 110 ℃; for 3h;

upstream raw materials:

para-bromobenzenethiol

(2S,3S,4R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester

bis(4-bromophenyl)disulfide

Downstream raw materials:

(2S,3R,4R)-3-carboxy-methyl-4-(4-bromophenylthio)-pyrrolidine-2-carboxylic acid

C₂₃H₂₉BF₃NO₇S

(2S,3R,4R)-3-carboxymethyl-4-(4-methylphenylthio)pyrrolidine-2-carboxylicacid

C₁₃H₁₄BrNO₄S*ClH

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