methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-3-methylphenyl]propanoate

Base Information

• Chemical Name: methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-3-methylphenyl]propanoate
• CAS No.: 850321-19-6
• Molecular Formula: C₂₆H₃₀N₂O₇S
• Molecular Weight: 514.599
• Mol file: 850321-19-6.mol

Synonyms:methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-3-methylphenyl]propanoate

Chemical Property of methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-3-methylphenyl]propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-3-methylphenyl]propanoate

There total 7 articles about methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-3-methylphenyl]propanoate 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: 62.0%

2-tert-butyl-5-chloro-1,1-dioxo-1,2-dihydro-1λ6-isothiazol-3-one (850314-47-5) + [4-((2S)-2-[(benzyloxy)carbonyl]amino-3-methoxy-3-oxopropyl)-2-methylphenyl]boronic acid (850321-18-5) → methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-3-methylphenyl]propanoate (850321-19-6)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; at 80 ℃; for 24h;

DOI:10.1021/jm0600904

Reference yield:

methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)propanoate (850321-16-3) → methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-3-methylphenyl]propanoate (850321-19-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / triethylamine; palladium acetate; O-(dicyclohexylphosphino)biphenyl / dioxane / 0.5 h / 80 °C

2: 80 percent / sodium periodate; ammonium acetate / tetrahydrofuran / 24 h / 25 °C

3: 62 percent / potassium carbonate; [1,1'-bis(diphenylphosphino)ferrocene]PdCl₂*CH₂Cl₂ / dioxane / 24 h / 80 °C

With ammonium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium periodate; O-(dicyclohexylphosphino)biphenyl; palladium diacetate; potassium carbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; 3: Suzuki coupling;

DOI:10.1021/jm0600904

Reference yield:

methyl (2Z)-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)acrylate (905281-17-6) → methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-3-methylphenyl]propanoate (850321-19-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / (R,R)-1,2-[(o-MeOPh)(Ph)P]2CH₂CH₂(1,5-cyclooctadiene)Rh*BF₄; H₂ / ethanol / 24 h / 2585.74 Torr

2: 91 percent / triethylamine; palladium acetate; O-(dicyclohexylphosphino)biphenyl / dioxane / 0.5 h / 80 °C

3: 80 percent / sodium periodate; ammonium acetate / tetrahydrofuran / 24 h / 25 °C

4: 62 percent / potassium carbonate; [1,1'-bis(diphenylphosphino)ferrocene]PdCl₂*CH₂Cl₂ / dioxane / 24 h / 80 °C

With ammonium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium periodate; (Z,Z)-cycloocta-1,5-diene(R,R-1,2-bis(2,5-diethylphospholanyl)benzene)rhodium(I) tetrafluoroborate; O-(dicyclohexylphosphino)biphenyl; hydrogen; palladium diacetate; potassium carbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; ethanol; 4: Suzuki coupling;

DOI:10.1021/jm0600904

upstream raw materials:

2-tert-butyl-5-chloro-1,1-dioxo-1,2-dihydro-1λ⁶-isothiazol-3-one

[4-((2S)-2-[(benzyloxy)carbonyl]amino-3-methoxy-3-oxopropyl)-2-methylphenyl]boronic acid

methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)propanoate

methyl (2Z)-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)acrylate

Downstream raw materials:

methyl (2S)-2-amino-3-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)-3-methylphenyl]propanoate

methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-3-methylphenyl]propanoate