1-[N²-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysyl]-4-(1,1-dimethylethoxycarbonyl)piperazine

Base Information

• Chemical Name: 1-[N²-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysyl]-4-(1,1-dimethylethoxycarbonyl)piperazine
• CAS No.: 162178-70-3
• Molecular Formula: C₄₂H₅₄Br₂N₆O₇
• Molecular Weight: 914.735

Synonyms:1-[N²-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysyl]-4-(1,1-dimethylethoxycarbonyl)piperazine

Chemical Property of 1-[N²-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysyl]-4-(1,1-dimethylethoxycarbonyl)piperazine

Chemical Property:

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Technology Process of 1-[N²-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysyl]-4-(1,1-dimethylethoxycarbonyl)piperazine

There total 7 articles about 1-[N²-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysyl]-4-(1,1-dimethylethoxycarbonyl)piperazine 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:

1-(1,1-dimethylethoxycarbonyl)piperazine hydrochloride + N2-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N6-(phenylmethoxycarbonyl)-L-lysine (162178-96-3) → 1-[N2-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N6-(phenylmethoxycarbonyl)-L-lysyl]-4-(1,1-dimethylethoxycarbonyl)piperazine (162178-70-3)

Guidance literature:

N²-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -15 ℃; for 0.25h;

1-(1,1-dimethylethoxycarbonyl)piperazine hydrochloride; In tetrahydrofuran; at -15 - 20 ℃;

DOI:10.1021/jm0490641

Reference yield:

(R)-4-amino-3,5-dibromophenylalanine (864739-06-0) → 1-[N2-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N6-(phenylmethoxycarbonyl)-L-lysyl]-4-(1,1-dimethylethoxycarbonyl)piperazine (162178-70-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 75 °C

2.1: isobutyl chloroformate; N-methylmorpholine / CH₂Cl₂ / 3 h / -15 - 20 °C

2.2: 134 g / CH₂Cl₂ / 2 h / -15 °C

3.1: 134 g / aq. potassium hydrogensulfate / CH₂Cl₂

4.1: N-methylmorpholine / tetrahydrofuran / 0.5 h / -15 °C

5.1: N-methylmorpholine; ClSiMe₃ / CH₂Cl₂ / 12 h / 20 °C

5.2: tetrahydrofuran; CH₂Cl₂ / 2 h / -15 °C

5.3: aq. potassium hydrogensulfate / tetrahydrofuran; CH₂Cl₂

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

6.2: tetrahydrofuran / -15 - 20 °C

With 4-methyl-morpholine; potassium hydrogensulfate; chloro-trimethyl-silane; isobutyl chloroformate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm0490641

Reference yield:

C12H18Br2N2O2Si → 1-[N2-[4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanyl]-N6-(phenylmethoxycarbonyl)-L-lysyl]-4-(1,1-dimethylethoxycarbonyl)piperazine (162178-70-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: isobutyl chloroformate; N-methylmorpholine / CH₂Cl₂ / 3 h / -15 - 20 °C

1.2: 134 g / CH₂Cl₂ / 2 h / -15 °C

2.1: 134 g / aq. potassium hydrogensulfate / CH₂Cl₂

3.1: N-methylmorpholine / tetrahydrofuran / 0.5 h / -15 °C

4.1: N-methylmorpholine; ClSiMe₃ / CH₂Cl₂ / 12 h / 20 °C

4.2: tetrahydrofuran; CH₂Cl₂ / 2 h / -15 °C

4.3: aq. potassium hydrogensulfate / tetrahydrofuran; CH₂Cl₂

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

5.2: tetrahydrofuran / -15 - 20 °C

With 4-methyl-morpholine; potassium hydrogensulfate; chloro-trimethyl-silane; isobutyl chloroformate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm0490641

upstream raw materials:

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

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

4-amino-3,5-dibromo-N-(1-oxo-4-phenylbutyl)-D-phenylalanine

p-amino-D-phenylalanine

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