N²-[4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine methyl ester

Base Information

• Chemical Name: N²-[4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine methyl ester
• CAS No.: 864739-07-1
• Molecular Formula: C₃₃H₃₈Br₂N₄O₆
• Molecular Weight: 746.496

Synonyms:N²-[4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine methyl ester

Chemical Property of N²-[4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine methyl ester

Chemical Property:

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Technology Process of N²-[4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine methyl ester

There total 6 articles about N²-[4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine 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: 92.0%

4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanine (864738-92-1) + methyl (2S)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate hydrochloride (27894-50-4) → N2-[4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanyl]-N6-(phenylmethoxycarbonyl)-L-lysine methyl ester (864739-07-1)

Guidance literature:

4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanine; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -15 ℃; for 0.25h;

methyl (2S)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate hydrochloride; In tetrahydrofuran; at -15 - 20 ℃;

DOI:10.1021/jm0490641

Reference yield:

(R)-4-amino-3,5-dibromophenylalanine (864739-06-0) → N2-[4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanyl]-N6-(phenylmethoxycarbonyl)-L-lysine methyl ester (864739-07-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 85 percent / thionyl chloride / 20 °C

2.1: N-methylmorpholine; isobutyl chloroformate / tetrahydrofuran / 0.25 h / -15 °C

2.2: 95 percent / tetrahydrofuran / -15 - 20 °C

3.1: 90 percent / aq. sodium hydroxide / tetrahydrofuran / 3 h / 20 °C

4.1: N-methylmorpholine; isobutyl chloroformate / tetrahydrofuran / 0.25 h / -15 °C

4.2: 92 percent / tetrahydrofuran / -15 - 20 °C

With 4-methyl-morpholine; sodium hydroxide; thionyl chloride; isobutyl chloroformate; In tetrahydrofuran;

DOI:10.1021/jm0490641

Reference yield:

4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanine methyl ester (878486-06-7) → N2-[4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanyl]-N6-(phenylmethoxycarbonyl)-L-lysine methyl ester (864739-07-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / aq. sodium hydroxide / tetrahydrofuran / 3 h / 20 °C

2.1: N-methylmorpholine; isobutyl chloroformate / tetrahydrofuran / 0.25 h / -15 °C

2.2: 92 percent / tetrahydrofuran / -15 - 20 °C

With 4-methyl-morpholine; sodium hydroxide; isobutyl chloroformate; In tetrahydrofuran;

DOI:10.1021/jm0490641

upstream raw materials:

4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanine

methyl (2S)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate hydrochloride

(R)-4-amino-3,5-dibromophenylalanine

4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanine methyl ester

Downstream raw materials:

N²-[4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine-2-phenethylamide

N²-[4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine

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