1-[(S)-O-5-isoquinolinesulfonyl-N-tert-butyloxycarbonyl-N-methyltyrosyl]-4-(4-fluorobenzyl)piperazine

Base Information

• Chemical Name: 1-[(S)-O-5-isoquinolinesulfonyl-N-tert-butyloxycarbonyl-N-methyltyrosyl]-4-(4-fluorobenzyl)piperazine
• CAS No.: 516473-22-6
• Molecular Formula: C₃₅H₃₉FN₄O₆S
• Molecular Weight: 662.782

Synonyms:1-[(S)-O-5-isoquinolinesulfonyl-N-tert-butyloxycarbonyl-N-methyltyrosyl]-4-(4-fluorobenzyl)piperazine

Chemical Property of 1-[(S)-O-5-isoquinolinesulfonyl-N-tert-butyloxycarbonyl-N-methyltyrosyl]-4-(4-fluorobenzyl)piperazine

Chemical Property:

Purity/Quality:

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Technology Process of 1-[(S)-O-5-isoquinolinesulfonyl-N-tert-butyloxycarbonyl-N-methyltyrosyl]-4-(4-fluorobenzyl)piperazine

There total 3 articles about 1-[(S)-O-5-isoquinolinesulfonyl-N-tert-butyloxycarbonyl-N-methyltyrosyl]-4-(4-fluorobenzyl)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: 77.0%

5-isoquinolinesulfonyl chloride (84468-15-5) + 1-[(S)-N-tert-butyloxycarbonyl-N-methyltyrosyl]-4-(4-fluorobenzyl)piperazine (516472-93-8) → 1-[(S)-O-5-isoquinolinesulfonyl-N-tert-butyloxycarbonyl-N-methyltyrosyl]-4-(4-fluorobenzyl)piperazine (516473-22-6)

Guidance literature:

1-[(S)-N-tert-butyloxycarbonyl-N-methyltyrosyl]-4-(4-fluorobenzyl)piperazine; With sodium hydride; In tetrahydrofuran; for 0.166667h;

5-isoquinolinesulfonyl chloride; In tetrahydrofuran; dichloromethane; at 20 ℃; for 18h;

DOI:10.1021/jm021049d

Reference yield:

1-(4-fluorophenylmethyl)piperazine (70931-28-1) → 1-[(S)-O-5-isoquinolinesulfonyl-N-tert-butyloxycarbonyl-N-methyltyrosyl]-4-(4-fluorobenzyl)piperazine (516473-22-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 78 percent / EDC; HOBt / dimethylformamide / 24 h / 20 °C

2.1: NaH / tetrahydrofuran / 0.17 h

2.2: 77 percent / tetrahydrofuran; CH₂Cl₂ / 18 h / 20 °C

With sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm021049d

Reference yield:

(S)-2-((tert-butoxycarbonyl)(methyl)amino)-3-(4-hydroxyphenyl)propanoic acid (82038-34-4) → 1-[(S)-O-5-isoquinolinesulfonyl-N-tert-butyloxycarbonyl-N-methyltyrosyl]-4-(4-fluorobenzyl)piperazine (516473-22-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 78 percent / EDC; HOBt / dimethylformamide / 24 h / 20 °C

2.1: NaH / tetrahydrofuran / 0.17 h

2.2: 77 percent / tetrahydrofuran; CH₂Cl₂ / 18 h / 20 °C

With sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm021049d

upstream raw materials:

5-isoquinolinesulfonyl chloride

1-[(S)-N-tert-butyloxycarbonyl-N-methyltyrosyl]-4-(4-fluorobenzyl)piperazine

1-(4-fluorophenylmethyl)piperazine

(S)-2-((tert-butoxycarbonyl)(methyl)amino)-3-(4-hydroxyphenyl)propanoic acid

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