N-{(2S,3S)-4-[(4R)-4-(tert-butylcarbamoyl)-1,3-thiazolidin-3-yl]-3-hydroxy-4-oxo-1-phenylbutan-2-yl}-N~2~-[(isoquinolin-5-yloxy)acetyl]-L-valinamide

Base Information

• Chemical Name: N-{(2S,3S)-4-[(4R)-4-(tert-butylcarbamoyl)-1,3-thiazolidin-3-yl]-3-hydroxy-4-oxo-1-phenylbutan-2-yl}-N~2~-[(isoquinolin-5-yloxy)acetyl]-L-valinamide
• CAS No.: 156880-90-9
• Molecular Formula: C34H43 N5 O6 S
• Molecular Weight: 649.8001
• Mol file: 156880-90-9.mol

Synonyms:4-Thiazolidinecarboxamide,N-(1,1-dimethylethyl)-3-[2-hydroxy-3-[[2-[[(5-isoquinolinyloxy)acetyl]amino]-3-methyl-1-oxobutyl]amino]-1-oxo-4-phenylbutyl]-,[4R-[3[2S*,3S*(S*)],4R*]]-; KNI 279

Chemical Property of N-{(2S,3S)-4-[(4R)-4-(tert-butylcarbamoyl)-1,3-thiazolidin-3-yl]-3-hydroxy-4-oxo-1-phenylbutan-2-yl}-N~2~-[(isoquinolin-5-yloxy)acetyl]-L-valinamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1007°C at 760 mmHg
• Flash Point: 562.8°C
• Density: 1.259g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-{(2S,3S)-4-[(4R)-4-(tert-butylcarbamoyl)-1,3-thiazolidin-3-yl]-3-hydroxy-4-oxo-1-phenylbutan-2-yl}-N~2~-[(isoquinolin-5-yloxy)acetyl]-L-valinamide

There total 9 articles about N-{(2S,3S)-4-[(4R)-4-(tert-butylcarbamoyl)-1,3-thiazolidin-3-yl]-3-hydroxy-4-oxo-1-phenylbutan-2-yl}-N~2~-[(isoquinolin-5-yloxy)acetyl]-L-valinamide 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:

(2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (62023-65-8,76498-21-0,77171-41-6,82848-28-0,105181-72-4,116661-86-0) → (R)-N-tert-butyl-3-[(2S,3S)-2-hydroxy-3-[(S)-2-(5-isoquinolinyloxyacetyl)amino-3-methylbutanoyl]amino-4-phenylbutanoyl]-1,3-thiazolidine-4-carboxamide (156880-90-9)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 85 percent / HCl / dioxane; CH₂Cl₂ / 2 h

3: 78 percent / 1-hydroxybenzotriazol; N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide*HCl / dimethylformamide

4: HCl / dioxane; CH₂Cl₂ / 2 h

5: 1-hydroxybenzotriazol; N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide*HCl; TEA / dimethylformamide

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

DOI:10.1248/cpb.48.1310

Reference yield:

(R)-N-tert-butyl-1,3-thiazolidine-4-carboxamide (128019-19-2) → (R)-N-tert-butyl-3-[(2S,3S)-2-hydroxy-3-[(S)-2-(5-isoquinolinyloxyacetyl)amino-3-methylbutanoyl]amino-4-phenylbutanoyl]-1,3-thiazolidine-4-carboxamide (156880-90-9)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 85 percent / HCl / dioxane; CH₂Cl₂ / 2 h

3: 78 percent / 1-hydroxybenzotriazol; N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide*HCl / dimethylformamide

4: HCl / dioxane; CH₂Cl₂ / 2 h

5: 1-hydroxybenzotriazol; N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide*HCl; TEA / dimethylformamide

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

DOI:10.1248/cpb.48.1310

Reference yield:

N-tert-butyl-3-(tert-butoxycarbonyl)thiazolidine-4-carboxamide (148982-94-9) → (R)-N-tert-butyl-3-[(2S,3S)-2-hydroxy-3-[(S)-2-(5-isoquinolinyloxyacetyl)amino-3-methylbutanoyl]amino-4-phenylbutanoyl]-1,3-thiazolidine-4-carboxamide (156880-90-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / HCl / dioxane; CH₂Cl₂ / 2 h

2: 1-hydroxybenzotriazol; N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide*HCl / dimethylformamide

3: 85 percent / HCl / dioxane; CH₂Cl₂ / 2 h

4: 78 percent / 1-hydroxybenzotriazol; N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide*HCl / dimethylformamide

5: HCl / dioxane; CH₂Cl₂ / 2 h

6: 1-hydroxybenzotriazol; N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide*HCl; TEA / dimethylformamide

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

DOI:10.1248/cpb.48.1310

upstream raw materials:

5-isoquinolinyloxyacetic acid

(R)-3-[(2S,3S)-3-((S)-2-Amino-3-methyl-butyrylamino)-2-hydroxy-4-phenyl-butyryl]-thiazolidine-4-carboxylic acid tert-butylamide

(2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid

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

Downstream raw materials:

3-{3(S)-[N-(N-methyl-1,2-dihydroisoquinolin-5-yloxyacetyl)-l-valinyl]amino-2(S)-hydroxy-4-phenylbutanoyl}-N-(tert-butyl)thiazolidine-4(R)-carboxamide

3-{3(S)-[N-(N-ethyl-1,2-dihydroisoquinolin-5-yloxyacetyl)-l-valinyl]amino-2(S)-hydroxy-4-phenylbutanoyl}-N-(tert-butyl)thiazolidine-4(R)-carboxamide