Methyl Ester of N-<3-<<3-<1-Oxo-2-(benzyloxycarbonyl)-2-hydroxyiminoethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline

Base Information

• Chemical Name: Methyl Ester of N-<3-<<3-<1-Oxo-2-(benzyloxycarbonyl)-2-hydroxyiminoethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline
• CAS No.: 86272-72-2
• Molecular Formula: C₃₃H₃₉N₃O₁₁
• Molecular Weight: 653.686
• Mol file: 86272-72-2.mol

Synonyms:Methyl Ester of N-<3-<<3-<1-Oxo-2-(benzyloxycarbonyl)-2-hydroxyiminoethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline

Chemical Property of Methyl Ester of N-<3-<<3-<1-Oxo-2-(benzyloxycarbonyl)-2-hydroxyiminoethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl Ester of N-<3-<<3-<1-Oxo-2-(benzyloxycarbonyl)-2-hydroxyiminoethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline

There total 6 articles about Methyl Ester of N-<3-<<3-<1-Oxo-2-(benzyloxycarbonyl)-2-hydroxyiminoethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline 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: 88.0%

Methyl Ester of N-<3-<<3-<1-Oxo-2-(benzyloxycarbonyl)ethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline (86272-71-1) → Methyl Ester of N-<3-<<3-<1-Oxo-2-(benzyloxycarbonyl)-2-hydroxyiminoethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline (86272-72-2)

Guidance literature:

With sodium nitrite; In water; acetic acid; at 0 ℃;

DOI:10.1021/jo00164a010

Reference yield:

benzyl prolinate hydrochloride (80089-24-3) → Methyl Ester of N-<3-<<3-<1-Oxo-2-(benzyloxycarbonyl)-2-hydroxyiminoethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline (86272-72-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 46.5 percent / N-methylmorpholine, N,N'-dicyclohexylcarbodiimide / CH₂Cl₂

2: 1.) H₂ / 1.) Pd/C / 1.) 1h; 2.) ethyl acetate/methanol, diethyl ether

3: 1.) m-dimethoxybenzene; 2.) di-tert-butyl dicarbonate, 1N KHCO₃ / 1.) trifluoroacetic acid, 0 deg C, 3h; 2.) dioxane

4: 87 percent / N,N-carbonyldiimidazole / tetrahydrofuran / 5 h / 50 °C

5: 88 percent / NaNO₂ / acetic acid; H₂O / 0 °C

With 4-methyl-morpholine; di-tert-butyl dicarbonate; hydrogen; potassium hydrogencarbonate; dicyclohexyl-carbodiimide; 1,1'-carbonyldiimidazole; 1,3-Dimethoxybenzene; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; acetic acid;

DOI:10.1021/jo00164a010

Reference yield:

Benzylic Ester of N-<3-<<3-(tert-Butoxycarbonyl)-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline (86272-67-5) → Methyl Ester of N-<3-<<3-<1-Oxo-2-(benzyloxycarbonyl)-2-hydroxyiminoethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline (86272-72-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) H₂ / 1.) Pd/C / 1.) 1h; 2.) ethyl acetate/methanol, diethyl ether

2: 1.) m-dimethoxybenzene; 2.) di-tert-butyl dicarbonate, 1N KHCO₃ / 1.) trifluoroacetic acid, 0 deg C, 3h; 2.) dioxane

3: 87 percent / N,N-carbonyldiimidazole / tetrahydrofuran / 5 h / 50 °C

4: 88 percent / NaNO₂ / acetic acid; H₂O / 0 °C

With di-tert-butyl dicarbonate; hydrogen; potassium hydrogencarbonate; 1,1'-carbonyldiimidazole; 1,3-Dimethoxybenzene; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; water; acetic acid;

DOI:10.1021/jo00164a010

upstream raw materials:

Methyl Ester of N-<3-<<3-<1-Oxo-2-(benzyloxycarbonyl)ethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline

benzyl prolinate hydrochloride

trans-N-(tert-Butoxycarbonyl)-3-<<3-(tert-butoxycarbonyl)-4-methoxyphenyl>oxy>proline

Methyl Ester of N-<3-<<3-(tert-Butoxycarbonyl)-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline

Downstream raw materials:

Methyl Ester of N-<3-<<3-<2-(Carbobenzoxyamino)-1-oxoethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline

N-<3-<<3-<2-(Carbobenzoxyamino)-1-hydroxyethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline

Methyl Ester of N-<3-<<3-<2-(Carbobenzoxyamino)-1-hydroxyethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline

cycloethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-prolyl>