(2S,4R)-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide

Base Information

• Chemical Name: (2S,4R)-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide
• CAS No.: 1448189-45-4
• Molecular Formula: C₁₆H₁₉N₃O₂S
• Molecular Weight: 317.412
• Mol file: 1448189-45-4.mol

Synonyms:(2S,4R)-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide

Chemical Property of (2S,4R)-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide

There total 14 articles about (2S,4R)-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide 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: 79.0%

tert‐butyl (2S,4R)‐4‐hydroxy‐2‐({[4‐(4‐methyl‐1,3‐thiazol‐5‐yl)phenyl]methyl}carbamoyl)pyrrolidine‐1‐carboxylate (1448191-54-5) → (2S,4R)-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide (1448189-45-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 1h;

DOI:10.1002/anie.201206231

Reference yield: 79.0%

(2S,4R)-tert-butyl 4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidine-1-carboxylate → (2S,4R)-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide (1448189-45-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 1h; Inert atmosphere;

Reference yield:

4-bromobenzenecarbonitrile (623-00-7) → (2S,4R)-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide (1448189-45-4)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium acetate; palladium diacetate / N,N-dimethyl acetamide / 19 h / 150 °C / Inert atmosphere

2: cobalt(II) chloride; sodium tetrahydroborate / methanol / 0 - 4 °C

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide; dichloromethane / 15 h

4: hydrogenchloride / 1,4-dioxane / 1 h

With hydrogenchloride; sodium tetrahydroborate; potassium acetate; palladium diacetate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; cobalt(II) chloride; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide;

DOI:10.1002/anie.201206231

upstream raw materials:

tert‐butyl (2S,4R)‐4‐hydroxy‐2‐({[4‐(4‐methyl‐1,3‐thiazol‐5‐yl)phenyl]methyl}carbamoyl)pyrrolidine‐1‐carboxylate

2-(trimethylsilyl)ethyl 4-bromobenzylcarbamate

2-(trimethylsilyl)ethyl 4-(4-methylthiazol-5-yl)benzylcarbamate

1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methaneamine

Downstream raw materials:

C₂₅H₂₇N₃O₄S

C₂₃H₂₂BrN₃O₃S

C₂₃H₂₁BrClN₃O₃S

C₂₄H₂₂N₄O₃S