(S)-2-[(1R,2R)-2-Benzyloxycarbonyl-1-(imidazole-1-carbothioyloxy)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-2-[(1R,2R)-2-Benzyloxycarbonyl-1-(imidazole-1-carbothioyloxy)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 173441-07-1
• Molecular Formula: C₂₄H₃₁N₃O₅S
• Molecular Weight: 473.593

Synonyms:(S)-2-[(1R,2R)-2-Benzyloxycarbonyl-1-(imidazole-1-carbothioyloxy)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of (S)-2-[(1R,2R)-2-Benzyloxycarbonyl-1-(imidazole-1-carbothioyloxy)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of (S)-2-[(1R,2R)-2-Benzyloxycarbonyl-1-(imidazole-1-carbothioyloxy)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 2 articles about (S)-2-[(1R,2R)-2-Benzyloxycarbonyl-1-(imidazole-1-carbothioyloxy)-propyl]-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: 59.0%

1,1'-Thiocarbonyldiimidazole (6160-65-2) + benzyl (2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate (163768-51-2) → (S)-2-[(1R,2R)-2-Benzyloxycarbonyl-1-(imidazole-1-carbothioyloxy)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (173441-07-1)

Guidance literature:

In 1,4-dioxane; for 24h; Ambient temperature;

DOI:10.1248/cpb.43.1706

Reference yield:

Boc-L-Pro-H (69610-41-9,117625-90-8) → (S)-2-[(1R,2R)-2-Benzyloxycarbonyl-1-(imidazole-1-carbothioyloxy)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (173441-07-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 18 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

2: 59 percent / dioxane / 24 h / Ambient temperature

With lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1248/cpb.43.1706

Reference yield: 81.0%

(S)-2-[(1R,2R)-2-Benzyloxycarbonyl-1-(imidazole-1-carbothioyloxy)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (173441-07-1) → benzyl (2R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-2-methylpropanoate (173441-06-0)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 110 ℃; for 4h;

DOI:10.1248/cpb.43.1706

upstream raw materials:

1,1'-Thiocarbonyldiimidazole

benzyl (2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate

Boc-L-Pro-H

Downstream raw materials:

benzyl (2R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-2-methylpropanoate

(R)-2-Methyl-N-((S)-2-phenyl-1-thiazol-2-yl-ethyl)-3-(S)-pyrrolidin-2-yl-propionamide

(S)-2-[(R)-2-((S)-2-Phenyl-1-thiazol-2-yl-ethylcarbamoyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

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