(1S,4R)-1-<3-(benzoylthio)-2-methyl-1-oxopropyl>-4-hydroxy-L-proline methyl ester

Base Information

• Chemical Name: (1S,4R)-1-<3-(benzoylthio)-2-methyl-1-oxopropyl>-4-hydroxy-L-proline methyl ester
• CAS No.: 80586-33-0
• Molecular Formula: C₁₇H₂₁NO₅S
• Molecular Weight: 351.423

Synonyms:(1S,4R)-1-<3-(benzoylthio)-2-methyl-1-oxopropyl>-4-hydroxy-L-proline methyl ester

Chemical Property of (1S,4R)-1-<3-(benzoylthio)-2-methyl-1-oxopropyl>-4-hydroxy-L-proline methyl ester

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Technology Process of (1S,4R)-1-<3-(benzoylthio)-2-methyl-1-oxopropyl>-4-hydroxy-L-proline methyl ester

There total 3 articles about (1S,4R)-1-<3-(benzoylthio)-2-methyl-1-oxopropyl>-4-hydroxy-L-proline methyl 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: 78.0%

methanol (67-56-1) + (1S,4R)-1-<3-(benzoylthio)-2-methyl-1-oxopropyl>-4-hydroxy-L-proline (81814-84-8) → (1S,4R)-1-<3-(benzoylthio)-2-methyl-1-oxopropyl>-4-hydroxy-L-proline methyl ester (80586-33-0)

Guidance literature:

With toluene-4-sulfonic acid; for 18h; Heating;

DOI:10.1021/jm00401a014

Reference yield:

3-(benzoylthio)-2(S)-methylpropionyl chloride (74654-91-4) → (1S,4R)-1-<3-(benzoylthio)-2-methyl-1-oxopropyl>-4-hydroxy-L-proline methyl ester (80586-33-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / 10percent sodium carbonate, pH 9.3 / H₂O; toluene / 1.5 h

2: 78 percent / p-TsOH / 18 h / Heating

With sodium carbonate; toluene-4-sulfonic acid; In water; toluene;

DOI:10.1021/jm00401a014

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → (1S,4R)-1-<3-(benzoylthio)-2-methyl-1-oxopropyl>-4-hydroxy-L-proline methyl ester (80586-33-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / 10percent sodium carbonate, pH 9.3 / H₂O; toluene / 1.5 h

2: 78 percent / p-TsOH / 18 h / Heating

With sodium carbonate; toluene-4-sulfonic acid; In water; toluene;

DOI:10.1021/jm00401a014

upstream raw materials:

methanol

(1S,4R)-1-<3-(benzoylthio)-2-methyl-1-oxopropyl>-4-hydroxy-L-proline

3-(benzoylthio)-2(S)-methylpropionyl chloride

4R-4-hydroxyproline

Downstream raw materials:

(4S)-1-[(S)-3-benzoylthio-2-methylpropanoyl]-4-phenylthio-L-proline methyl ester

(2S,4S)-1-((S)-3-Benzoylsulfanyl-2-methyl-propionyl)-4-(naphthalen-2-yloxy)-pyrrolidine-2-carboxylic acid methyl ester

Zofenoprilat

(2S,4S)-4-(4-Fluoro-phenylsulfanyl)-1-((S)-3-mercapto-2-methyl-propionyl)-pyrrolidine-2-carboxylic acid

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