methyl N-acetyl-4(S)-(benzylthio)pyrrolidine-2(S)-carboxylate

Base Information

• Chemical Name: methyl N-acetyl-4(S)-(benzylthio)pyrrolidine-2(S)-carboxylate
• CAS No.: 78854-22-5
• Molecular Formula: C₁₅H₁₉NO₃S
• Molecular Weight: 293.387
• Mol file: 78854-22-5.mol

Synonyms:methyl N-acetyl-4(S)-(benzylthio)pyrrolidine-2(S)-carboxylate

Chemical Property of methyl N-acetyl-4(S)-(benzylthio)pyrrolidine-2(S)-carboxylate

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of methyl N-acetyl-4(S)-(benzylthio)pyrrolidine-2(S)-carboxylate

There total 1 articles about methyl N-acetyl-4(S)-(benzylthio)pyrrolidine-2(S)-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: 69.0%

phenylmethanethiol (100-53-8) + (3R,5S)-5-(methoxycarbonyl)-1-acetylpyrrolidin-3-yl 4-methylbenzenesulfonate (57750-51-3) → methyl N-acetyl-4(S)-(benzylthio)pyrrolidine-2(S)-carboxylate (78854-22-5)

Guidance literature:

With sodium; In ethanol; at 25 ℃; for 20.5h;

DOI:10.1021/jo00334a015

Reference yield:

methyl N-acetyl-4(S)-(benzylthio)pyrrolidine-2(S)-carboxylate (78854-22-5) → N-acetyl-4(S)-(benzylthio)pyrrolidine-2(S)-carboxic acid (78854-23-6)

Guidance literature:

With sodium hydroxide; In methanol; at 0 ℃; for 16h; Yield given;

DOI:10.1021/jo00334a015

Reference yield:

methyl N-acetyl-4(S)-(benzylthio)pyrrolidine-2(S)-carboxylate (78854-22-5) → 4(S)-(benzylthio)pyrrolidine-2(S)-carboxylic acid hydrochloride (78854-26-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1N aq. NaOH / methanol / 16 h / 0 °C

2: 90 percent / 3N HCl / H₂O / 8 h / Heating

With hydrogenchloride; sodium hydroxide; In methanol; water;

DOI:10.1021/jo00334a015

upstream raw materials:

phenylmethanethiol

(3R,5S)-5-(methoxycarbonyl)-1-acetylpyrrolidin-3-yl 4-methylbenzenesulfonate

Downstream raw materials:

N-acetyl-4(S)-(benzylthio)pyrrolidine-2(S)-carboxic acid

(4S)-4-mercapto-L-proline hydrochloride

4(S)-(benzylthio)pyrrolidine-2(S)-carboxylic acid hydrochloride