(2S,4R)-2-((S)-1-Methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-4-(2-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2S,4R)-2-((S)-1-Methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-4-(2-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 1026163-04-1
• Molecular Formula: C₂₃H₃₄N₂O₆S
• Molecular Weight: 466.599

Synonyms:(2S,4R)-2-((S)-1-Methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-4-(2-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of (2S,4R)-2-((S)-1-Methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-4-(2-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (2S,4R)-2-((S)-1-Methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-4-(2-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 6 articles about (2S,4R)-2-((S)-1-Methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-4-(2-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl 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: 94.0%

(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride (2491-18-1) + (2S,4R)-4-(2-Methoxy-phenyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (1026917-85-0) → (2S,4R)-2-((S)-1-Methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-4-(2-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1026163-04-1)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.48.740

Reference yield:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → (2S,4R)-2-((S)-1-Methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-4-(2-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1026163-04-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: LiN[Si(CH₃)3]2 / tetrahydrofuran / -78 °C

2.2: 30 percent / tetrahydrofuran / -78 - 20 °C

3.1: (PhCH₂)(Cl)Pd(PPh₃)2; LiCl; aq. Na₂CO₃ / 1,2-dimethoxy-ethane / 86 °C

4.1: 100 percent / H₂ / 5 percent Pd/C / ethyl acetate

5.1: aq. LiOH / dioxane / 0 - 20 °C

6.1: 94 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; HOBt*H₂O; N-methylmorpholine / dimethylformamide

With 4-methyl-morpholine; lithium hydroxide; oxalyl dichloride; trans benzyl(chloro)bis(triphenylphosphine)palladium(II); hydrogen; sodium carbonate; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium chloride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.1: Oxidation / 2.1: Enolization / 2.2: Triflation / 3.1: Arylation / 4.1: Catalytic hydrogenation / 5.1: Hydrolysis / 6.1: Acylation;

DOI:10.1248/cpb.48.740

Reference yield:

(S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate (102195-80-2) → (2S,4R)-2-((S)-1-Methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-4-(2-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1026163-04-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: LiN[Si(CH₃)3]2 / tetrahydrofuran / -78 °C

1.2: 30 percent / tetrahydrofuran / -78 - 20 °C

2.1: (PhCH₂)(Cl)Pd(PPh₃)2; LiCl; aq. Na₂CO₃ / 1,2-dimethoxy-ethane / 86 °C

3.1: 100 percent / H₂ / 5 percent Pd/C / ethyl acetate

4.1: aq. LiOH / dioxane / 0 - 20 °C

5.1: 94 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; HOBt*H₂O; N-methylmorpholine / dimethylformamide

With 4-methyl-morpholine; lithium hydroxide; trans benzyl(chloro)bis(triphenylphosphine)palladium(II); hydrogen; sodium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium chloride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; ethyl acetate; N,N-dimethyl-formamide; 1.1: Enolization / 1.2: Triflation / 2.1: Arylation / 3.1: Catalytic hydrogenation / 4.1: Hydrolysis / 5.1: Acylation;

DOI:10.1248/cpb.48.740

upstream raw materials:

(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride

(2S,4R)-4-(2-Methoxy-phenyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

(S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate

Downstream raw materials:

C₂₉H₄₃N₃O₈S₃

C₃₀H₄₅N₃O₈S₃

(R)-4-{(E)-3-[(2S,4R)-2-((S)-1-Methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-4-(2-methoxy-phenyl)-pyrrolidin-1-yl]-propenyl}-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester

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