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

Base Information

• Chemical Name: N²-[4-amino-3,5-dibromo-N-(1,1-dimethylethoxycarbonyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine-2-phenethylamide
• CAS No.: 864738-88-5
• Molecular Formula: C₃₆H₄₅Br₂N₅O₆
• Molecular Weight: 803.591

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

Chemical Property of N²-[4-amino-3,5-dibromo-N-(1,1-dimethylethoxycarbonyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine-2-phenethylamide

Chemical Property:

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Technology Process of N²-[4-amino-3,5-dibromo-N-(1,1-dimethylethoxycarbonyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine-2-phenethylamide

There total 4 articles about N²-[4-amino-3,5-dibromo-N-(1,1-dimethylethoxycarbonyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine-2-phenethylamide 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: 82.0%

(R)-3-(4-amino-3,5-dibromo-phenyl)-2-tert-butoxycarbonylamino-propionic acid + N6-(phenylmethoxycarbonyl)-L-lysine-2-phenethylamide (246514-90-9) → N2-[4-amino-3,5-dibromo-N-(1,1-dimethylethoxycarbonyl)-D-phenylalanyl]-N6-(phenylmethoxycarbonyl)-L-lysine-2-phenethylamide (864738-88-5)

Guidance literature:

(R)-3-(4-amino-3,5-dibromo-phenyl)-2-tert-butoxycarbonylamino-propionic acid; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -15 ℃; for 0.25h;

N⁶-(phenylmethoxycarbonyl)-L-lysine-2-phenethylamide; In tetrahydrofuran; at -15 - 20 ℃;

DOI:10.1021/jm0490641

Reference yield:

Boc-Lys(Z)-OH (2389-45-9) → N2-[4-amino-3,5-dibromo-N-(1,1-dimethylethoxycarbonyl)-D-phenylalanyl]-N6-(phenylmethoxycarbonyl)-L-lysine-2-phenethylamide (864738-88-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 92 percent / diisopropylethylamine; TBTU; HOBt / dimethylformamide / 20 °C

2.1: 99 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / 20 °C

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

3.2: 82 percent / tetrahydrofuran / -15 - 20 °C

With 4-methyl-morpholine; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0490641

Reference yield:

phenethylamine (64-04-0) → N2-[4-amino-3,5-dibromo-N-(1,1-dimethylethoxycarbonyl)-D-phenylalanyl]-N6-(phenylmethoxycarbonyl)-L-lysine-2-phenethylamide (864738-88-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 92 percent / diisopropylethylamine; TBTU; HOBt / dimethylformamide / 20 °C

2.1: 99 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / 20 °C

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

3.2: 82 percent / tetrahydrofuran / -15 - 20 °C

With 4-methyl-morpholine; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0490641

upstream raw materials:

N⁶-(phenylmethoxycarbonyl)-L-lysine-2-phenethylamide

Boc-Lys(Z)-OH

phenethylamine

N²-(1,1-dimethylethoxycarbonyl)-N⁶-(phenylmethoxycarbonyl)-L-lysine-2-phenethylamide

Downstream raw materials:

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

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