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

Base Information

Chemical Name:(2S,4R)-2-((S)-1-Methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:1027899-77-9
Molecular Formula:C₂₂H₃₂N₂O₅S
Molecular Weight:436.572
Hs Code.:

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

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

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

There total 6 articles about (2S,4R)-2-((S)-1-Methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-4-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%

: 2491-18-1
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride

: 336818-78-1,158567-91-0
(2S,4R)-1-(tert-butoxycarbonyl)-4-phenyl-2-pyrrolidinecarboxylic acid

: 1027899-77-9
(2S,4R)-2-((S)-1-Methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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:

: 74844-91-0
1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

: 1027899-77-9
(2S,4R)-2-((S)-1-Methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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: Phenylation / 4.1: Catalytic hydrogenation / 5.1: Hydrolysis / 6.1: Acylation;
DOI:10.1248/cpb.48.740

Reference yield:

: 102195-80-2
(S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate

: 1027899-77-9
(2S,4R)-2-((S)-1-Methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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: Phenylation / 3.1: Catalytic hydrogenation / 4.1: Hydrolysis / 5.1: Acylation;
DOI:10.1248/cpb.48.740