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

Base Information

• Chemical Name: Benzylic Ester of N-<3-<<3-(tert-Butoxycarbonyl)-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline
• CAS No.: 86272-67-5
• Molecular Formula: C₃₄H₄₄N₂O₉
• Molecular Weight: 624.731
• Mol file: 86272-67-5.mol

Synonyms:

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

There total 1 articles about Benzylic Ester of N-<3-<<3-(tert-Butoxycarbonyl)-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: 46.5%

benzyl prolinate hydrochloride (80089-24-3) + trans-N-(tert-Butoxycarbonyl)-3-<<3-(tert-butoxycarbonyl)-4-methoxyphenyl>oxy>proline (86272-66-4) → Benzylic Ester of N-<3-<<3-(tert-Butoxycarbonyl)-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline (86272-67-5) + Benzylic Ester of N-<3-<<3-(tert-Butoxycarbonyl)-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2R,3R)-prolyl>-(S)-proline (86272-68-6)

Guidance literature:

With 4-methyl-morpholine; dicyclohexyl-carbodiimide; In dichloromethane;

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) → Pentafluorophenyl Ester of N-<3-<<3-<2-(Carbobenzoxyamino)-1-hydroxyethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline (86272-76-6,86333-65-5)

Guidance literature:

Multi-step reaction with 8 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

5: 1.)H₂; 2.) 1N KHCO₃ / 1.) Pd/C / 1.) acetic acid, 5h; 2.) dioxane, room temp.

6: 98 percent / NaCNBH₃ / tetrahydrofuran; acetic acid

7: 83 percent / 1N LiOH / dioxane

8: 90 percent / DCC / ethyl acetate / 1.) 0 deg C, 1h; 2.) room temp., 1h

With lithium hydroxide; di-tert-butyl dicarbonate; hydrogen; sodium cyanoborohydride; potassium hydrogencarbonate; dicyclohexyl-carbodiimide; 1,1'-carbonyldiimidazole; 1,3-Dimethoxybenzene; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; water; acetic acid; ethyl acetate;

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)ethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline (86272-71-1)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/jo00164a010

upstream raw materials:

benzyl prolinate hydrochloride

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

Downstream raw materials:

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

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

Methyl Ester of N-<3-<<3-<1-Oxo-2-(benzyloxycarbonyl)ethyl>-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