2-allyl-3-isobutyl-N⁴-(1-methylcarbamoyl-2-phenyl-ethyl)-N¹-(tetrahydro-pyran-2-yloxy)-succinamide

Base Information

• Chemical Name: 2-allyl-3-isobutyl-N⁴-(1-methylcarbamoyl-2-phenyl-ethyl)-N¹-(tetrahydro-pyran-2-yloxy)-succinamide
• CAS No.: 474974-03-3
• Molecular Formula: C₂₆H₃₉N₃O₅
• Molecular Weight: 473.613

Synonyms:2-allyl-3-isobutyl-N⁴-(1-methylcarbamoyl-2-phenyl-ethyl)-N¹-(tetrahydro-pyran-2-yloxy)-succinamide

Chemical Property of 2-allyl-3-isobutyl-N⁴-(1-methylcarbamoyl-2-phenyl-ethyl)-N¹-(tetrahydro-pyran-2-yloxy)-succinamide

Chemical Property:

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Technology Process of 2-allyl-3-isobutyl-N⁴-(1-methylcarbamoyl-2-phenyl-ethyl)-N¹-(tetrahydro-pyran-2-yloxy)-succinamide

There total 3 articles about 2-allyl-3-isobutyl-N⁴-(1-methylcarbamoyl-2-phenyl-ethyl)-N¹-(tetrahydro-pyran-2-yloxy)-succinamide 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: 84.0%

O-2-tetrahydro-2H-pyranhydroxylamine (6723-30-4) + (2R,3S)-2-Isobutyl-3-(2-oxo-oxazolidine-3-carbonyl)-hex-5-enoic acid ((S)-1-methylcarbamoyl-2-phenyl-ethyl)-amide (474974-00-0) → 2-allyl-3-isobutyl-N4-(1-methylcarbamoyl-2-phenyl-ethyl)-N1-(tetrahydro-pyran-2-yloxy)-succinamide (474974-03-3)

Guidance literature:

With samarium(III) trifluoromethanesulfonate; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/ol026331t

Reference yield:

L-phenylalanine methylamide (35373-92-3) → 2-allyl-3-isobutyl-N4-(1-methylcarbamoyl-2-phenyl-ethyl)-N1-(tetrahydro-pyran-2-yloxy)-succinamide (474974-03-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenztriazole; CuCl₂ / dimethylformamide / 0.5 h / 0 °C

1.2: 36 percent / dimethylformamide / 15 h / 20 °C

2.1: 84 percent / samarium(III) triflate / tetrahydrofuran / 2 h / 20 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; copper dichloride; samarium(III) trifluoromethanesulfonate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ol026331t

Reference yield:

(2R,3S)-2-Isobutyl-3-(2-oxo-oxazolidine-3-carbonyl)-hex-5-enoic acid → 2-allyl-3-isobutyl-N4-(1-methylcarbamoyl-2-phenyl-ethyl)-N1-(tetrahydro-pyran-2-yloxy)-succinamide (474974-03-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenztriazole; CuCl₂ / dimethylformamide / 0.5 h / 0 °C

1.2: 36 percent / dimethylformamide / 15 h / 20 °C

2.1: 84 percent / samarium(III) triflate / tetrahydrofuran / 2 h / 20 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; copper dichloride; samarium(III) trifluoromethanesulfonate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ol026331t

upstream raw materials:

O-2-tetrahydro-2H-pyranhydroxylamine

(2R,3S)-2-Isobutyl-3-(2-oxo-oxazolidine-3-carbonyl)-hex-5-enoic acid ((S)-1-methylcarbamoyl-2-phenyl-ethyl)-amide

L-phenylalanine methylamide

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