(S)-2-[(2R,3R)-3-(4-Bromo-phenylamino)-2-hydroxy-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester

Base Information

• Chemical Name: (S)-2-[(2R,3R)-3-(4-Bromo-phenylamino)-2-hydroxy-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester
• CAS No.: 261957-97-5
• Molecular Formula: C₂₂H₂₇BrN₂O₄
• Molecular Weight: 463.371

Synonyms:(S)-2-[(2R,3R)-3-(4-Bromo-phenylamino)-2-hydroxy-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester

Chemical Property of (S)-2-[(2R,3R)-3-(4-Bromo-phenylamino)-2-hydroxy-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester

Chemical Property:

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Technology Process of (S)-2-[(2R,3R)-3-(4-Bromo-phenylamino)-2-hydroxy-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester

There total 1 articles about (S)-2-[(2R,3R)-3-(4-Bromo-phenylamino)-2-hydroxy-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester 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:

4-bromo-aniline (106-40-1) + CA-Leu-OMe → (S)-2-[(2S,3R)-3-(4-Bromo-phenylamino)-2-hydroxy-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester + (S)-2-[(2R,3R)-3-(4-Bromo-phenylamino)-2-hydroxy-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester (261957-97-5) + (S)-2-[(2S,3S)-3-(4-Bromo-phenylamino)-2-hydroxy-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester + (S)-2-[(2R,3S)-3-(4-Bromo-phenylamino)-2-hydroxy-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester

Guidance literature:

With polyaniline supported Co(II) salen; oxygen; isobutyraldehyde; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1) CH₃CN, RT, 20 h, 2) CH₃CN, 15 h, 25 deg C;

DOI:10.1016/S0040-4039(97)10172-1

Reference yield: 54.0%

(S)-2-[(2R,3R)-3-(4-Bromo-phenylamino)-2-hydroxy-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester (261957-97-5) → (S)-2-{[(2S,3R)-1-(4-Bromo-phenyl)-3-phenyl-aziridine-2-carbonyl]-amino}-4-methyl-pentanoic acid methyl ester

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In acetonitrile; at 20 ℃; for 25h;

Reference yield:

(S)-2-[(2R,3R)-3-(4-Bromo-phenylamino)-2-hydroxy-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester (261957-97-5) → (S)-2-[(2S,3S)-2-(4-Bromo-phenylamino)-3-hydroxy-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / diethyl azodicarboxylate; PPh₃ / acetonitrile / 25 h / 20 °C

2: 92 percent / aq. p-TsOH / tetrahydrofuran / 10 h / 20 °C

With toluene-4-sulfonic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; acetonitrile; 1: Cyclization / 2: ring opening;

upstream raw materials:

4-bromo-aniline

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