(R)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(tert-butoxycarbonyl)amino-3-methylbutanoyl]amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide

Base Information

• Chemical Name: (R)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(tert-butoxycarbonyl)amino-3-methylbutanoyl]amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide
• CAS No.: 305129-93-5
• Molecular Formula: C₃₀H₄₈N₄O₆S
• Molecular Weight: 592.8
• Mol file: 305129-93-5.mol

Synonyms:(R)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(tert-butoxycarbonyl)amino-3-methylbutanoyl]amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide

Chemical Property of (R)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(tert-butoxycarbonyl)amino-3-methylbutanoyl]amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(tert-butoxycarbonyl)amino-3-methylbutanoyl]amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide

There total 5 articles about (R)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(tert-butoxycarbonyl)amino-3-methylbutanoyl]amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-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: 94.0%

t-Boc-L-valine (13734-41-3) + (R)-N-tert-butyl-3-<(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl>-5,5-dimethyl-1,3-thiazolidine-4-carboxamide (184955-18-8) → (R)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(tert-butoxycarbonyl)amino-3-methylbutanoyl]amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide (305129-93-5)

Guidance literature:

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

DOI:10.1248/cpb.48.1310

Reference yield:

(R)-N-tert-butyl-5,5-dimethyl-1,3-thiazolidine-4-carboxamide (158941-58-3) → (R)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(tert-butoxycarbonyl)amino-3-methylbutanoyl]amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide (305129-93-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1-hydroxybenzotriazol; N,N'-dicyclohexylcarbodiimide / ethyl acetate

2: HCl / dioxane; CH₂Cl₂ / 2 h

3: 94 percent / 1-hydroxybenzotriazol; N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide*HCl / dimethylformamide

With hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1248/cpb.48.1310

Reference yield:

(R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid (117918-23-7) → (R)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(tert-butoxycarbonyl)amino-3-methylbutanoyl]amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide (305129-93-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: TEA; diphenylphosphoryl chloride / ethyl acetate / 1 h

1.2: ethyl acetate

2.1: HCl / dioxane; CH₂Cl₂ / 2 h

3.1: 1-hydroxybenzotriazol; N,N'-dicyclohexylcarbodiimide / ethyl acetate

4.1: HCl / dioxane; CH₂Cl₂ / 2 h

5.1: 94 percent / 1-hydroxybenzotriazol; N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide*HCl / dimethylformamide

With hydrogenchloride; TEA; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; Diphenylphosphinic chloride; In 1,4-dioxane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1248/cpb.48.1310

upstream raw materials:

t-Boc-L-valine

(R)-N-tert-butyl-3-<(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl>-5,5-dimethyl-1,3-thiazolidine-4-carboxamide

(R)-N-tert-butyl-5,5-dimethyl-1,3-thiazolidine-4-carboxamide

(R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

Downstream raw materials:

(R)-N-tert-butyl-3-{(2S,3S)-2-hydroxy-3-[(S)-2-(3-dimethylaminophenoxyacetyl)amino-3-methylbutanoyl]amino-4-phenylbutanoyl}-5,5-dimethyl-1,3-thiazolidine-4-carboxamide