1-[(N-tert-butoxycarbonyl-D-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-4-chloro-D-phenylalanyl]-4-phenylpiperazine

Base Information

• Chemical Name: 1-[(N-tert-butoxycarbonyl-D-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-4-chloro-D-phenylalanyl]-4-phenylpiperazine
• CAS No.: 668980-39-0
• Molecular Formula: C₃₄H₃₉ClN₄O₄
• Molecular Weight: 603.161
• Mol file: 668980-39-0.mol

Synonyms:1-[(N-tert-butoxycarbonyl-D-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-4-chloro-D-phenylalanyl]-4-phenylpiperazine

Chemical Property of 1-[(N-tert-butoxycarbonyl-D-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-4-chloro-D-phenylalanyl]-4-phenylpiperazine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(N-tert-butoxycarbonyl-D-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-4-chloro-D-phenylalanyl]-4-phenylpiperazine

There total 8 articles about 1-[(N-tert-butoxycarbonyl-D-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-4-chloro-D-phenylalanyl]-4-phenylpiperazine 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: 100.0%

4-phenyl-1-piperazine (92-54-6) + (N-tert-butoxycarbonyl-D-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-4-chloro-D-phenylalanine (252008-71-2) → 1-[(N-tert-butoxycarbonyl-D-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-4-chloro-D-phenylalanyl]-4-phenylpiperazine (668980-39-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/jm0311285

Reference yield:

N-Boc-D-(4-Cl)Phe-OH (57292-44-1) → 1-[(N-tert-butoxycarbonyl-D-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-4-chloro-D-phenylalanyl]-4-phenylpiperazine (668980-39-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / TEA / ethyl acetate / 7 h / Heating

2: 96 percent / AcOH; HCl / dioxane / 1 h / 20 °C

3: 99 percent / HATU; DIEA / dimethylformamide / 2 h / 20 °C

4: 100 percent / aq. NaOH / methanol / 1 h / 20 °C

5: 100 percent / HATU; DIEA / dimethylformamide / 2 h / 20 °C

With hydrogenchloride; sodium hydroxide; TEA; acetic acid; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1,4-dioxane; methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm0311285

Reference yield:

D-N-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinolinoline-3-carboxylic acid (78879-20-6,144069-68-1,115962-35-1) → 1-[(N-tert-butoxycarbonyl-D-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-4-chloro-D-phenylalanyl]-4-phenylpiperazine (668980-39-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / HATU; DIEA / dimethylformamide / 2 h / 20 °C

2: 100 percent / aq. NaOH / methanol / 1 h / 20 °C

3: 100 percent / HATU; DIEA / dimethylformamide / 2 h / 20 °C

With sodium hydroxide; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm0311285

upstream raw materials:

4-phenyl-1-piperazine

(N-tert-butoxycarbonyl-D-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-4-chloro-D-phenylalanine

N-Boc-D-(4-Cl)Phe-OH

D-N-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinolinoline-3-carboxylic acid

Downstream raw materials:

1-[(N-tert-butoxycarbonyl-D-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-4-chloro-D-phenylalanyl]-4-oxy-4-phenylpiperazine