benzyl 1-(4-{[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]methoxy}benzyl)-5-oxo-L-prolyl-3-trityl-L-histidinate

Base Information

• Chemical Name: benzyl 1-(4-{[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]methoxy}benzyl)-5-oxo-L-prolyl-3-trityl-L-histidinate
• CAS No.: 1422064-22-9
• Molecular Formula: C₅₅H₅₉N₅O₈
• Molecular Weight: 918.102

Synonyms:benzyl 1-(4-{[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]methoxy}benzyl)-5-oxo-L-prolyl-3-trityl-L-histidinate

Chemical Property of benzyl 1-(4-{[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]methoxy}benzyl)-5-oxo-L-prolyl-3-trityl-L-histidinate

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Technology Process of benzyl 1-(4-{[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]methoxy}benzyl)-5-oxo-L-prolyl-3-trityl-L-histidinate

There total 9 articles about benzyl 1-(4-{[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]methoxy}benzyl)-5-oxo-L-prolyl-3-trityl-L-histidinate 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: 60.0%

1-(4-{[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]methoxy}benzyl)-5-oxo-L-proline (1422064-21-8) + benzyl Np-trityl-L-histidinate → benzyl 1-(4-{[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]methoxy}benzyl)-5-oxo-L-prolyl-3-trityl-L-histidinate (1422064-22-9)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0 - 20 ℃; for 19h;

DOI:10.3390/molecules18010050

Reference yield:

methyl (S)-pyroglutamate (4931-66-2) → benzyl 1-(4-{[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]methoxy}benzyl)-5-oxo-L-prolyl-3-trityl-L-histidinate (1422064-22-9)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydride / tetrahydrofuran; paraffin oil / 24.25 h / 0 - 20 °C / Inert atmosphere

2: palladium 10% on activated carbon; hydrogen / methanol / 760.05 Torr

3: diethylazodicarboxylate; triphenylphosphine / toluene / 15 h / Reflux; Inert atmosphere

4: sodium hydroxide; water / methanol / 20 °C

5: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 19 h / 0 - 20 °C

With palladium 10% on activated carbon; water; hydrogen; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; toluene; paraffin oil;

DOI:10.3390/molecules18010050

Reference yield:

4-(benzyloxy)benzyl bromide (5544-60-5) → benzyl 1-(4-{[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]methoxy}benzyl)-5-oxo-L-prolyl-3-trityl-L-histidinate (1422064-22-9)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydride / tetrahydrofuran; paraffin oil / 24.25 h / 0 - 20 °C / Inert atmosphere

2: palladium 10% on activated carbon; hydrogen / methanol / 760.05 Torr

3: diethylazodicarboxylate; triphenylphosphine / toluene / 15 h / Reflux; Inert atmosphere

4: sodium hydroxide; water / methanol / 20 °C

5: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 19 h / 0 - 20 °C

With palladium 10% on activated carbon; water; hydrogen; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; toluene; paraffin oil;

DOI:10.3390/molecules18010050

upstream raw materials:

methyl (S)-pyroglutamate

methyl 1-[4-(benzyloxy)benzyl]-5-oxo-L-prolinate

4-(benzyloxy)benzyl bromide

methyl 1-(4-hydroxybenzyl)-5-oxo-L-prolinate

Downstream raw materials:

1-(4-{[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]methoxy}benzyl)-5-oxo-L-prolyl-L-histidine

1-(4-{[(2S)-2-ammonio-3-hydroxypropyl]oxy}benzyl)-5-oxo-L-prolyl-L-histidine hydrochloride

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