(2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide

Base Information

• Chemical Name: (2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide
• CAS No.: 1448297-52-6
• Molecular Formula: C₂₂H₃₀N₄O₃S
• Molecular Weight: 430.571
• Mol file: 1448297-52-6.mol

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

Chemical Property of (2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide

Chemical Property:

• Boiling Point: 691.6±55.0 °C(Predicted)
• PKA: 14.10±0.40(Predicted)
• Density: 1.254±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

99.3% ^*data from raw suppliers

(2S,4R)-1-((S)-2-Amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide

There total 16 articles about (2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)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: 97.0%

tert‐butyl N‐[(2S)‐1‐[(2S,4R)‐4‐hydroxy‐2‐({[4‐(4‐methyl‐1,3‐thiazol‐5‐yl)phenyl]methyl}carbamoyl)pyrrolidin‐1‐yl]‐3,3‐dimethyl‐1‐oxobutan‐2‐yl]carbamate (1448189-98-7) → (2S,4R)-1-[(2S)-2-azanyl-3,3-dimethylbutanoyl]-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]-4-oxidanylpyrrolidine-2-carboxamide (1448297-52-6)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; dichloromethane; at 0 - 20 ℃; for 1.5h;

Reference yield: 88.0%

(2S,4R)-1-[(2S)-2-[(tert-butoxycarbonyl)amino]-3,3-dimethylbutanoyl]-4-hydroxypyrrolidine-2-carboxylic acid (630421-46-4) + (4-(4-methylthiazol-5-yl)phenyl)methanamine trifluoroacetic acid salt → (2S,4R)-1-[(2S)-2-azanyl-3,3-dimethylbutanoyl]-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]-4-oxidanylpyrrolidine-2-carboxamide (1448297-52-6)

Guidance literature:

(2S,4R)-1-[(2S)-2-[(tert-butoxycarbonyl)amino]-3,3-dimethylbutanoyl]-4-hydroxypyrrolidine-2-carboxylic acid; (4-(4-methylthiazol-5-yl)phenyl)methanamine trifluoroacetic acid salt; With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃;

With trifluoroacetic acid; In dichloromethane; at 20 ℃;

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (2S,4R)-1-[(2S)-2-azanyl-3,3-dimethylbutanoyl]-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]-4-oxidanylpyrrolidine-2-carboxamide (1448297-52-6)

Guidance literature:

Multi-step reaction with 4 steps

1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C

2: lithium hydroxide / water; tetrahydrofuran / 20 °C

3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C

4: trifluoroacetic acid / dichloromethane / 20 °C

With N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium hydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.8b01631

upstream raw materials:

(2S,4R)-1-[(2S)-2-[(tert-butoxycarbonyl)amino]-3,3-dimethylbutanoyl]-4-hydroxypyrrolidine-2-carboxylic acid

methyl (2S_.4R)-1-[(2S)-2-{[(tert-butoxy)carbonyl]amino}-3.3-dimethylbutanoyl]-4-hydroxypyrrolidine-2-carboxylate

N-tert-butyloxycarbonyl-L-tert-leucine

L-4-hydroxyproline methyl ester hydrochloride

Refernces

• 1、 -. "Compound targeting ubiquitination degradation tyrosinase as well as preparation method and application thereof". . . Retrieved 2021/09/08.
• 2、 -. "Compound for targeted ubiquitination degradation of ERRalpha protein and pharmaceutical composition and application thereof". Paragraph 0234-0235; 0257-0259. . Retrieved 2020/06/20.