(5S,8R,9R)-5-Benzyl-1,2-dihydro-N^α-(N,N-dimethyl-L-alanyl-L-valyl)-N^α,9-ethylene-p-phencyclopeptine

Base Information

• Chemical Name: (5S,8R,9R)-5-Benzyl-1,2-dihydro-N^α-(N,N-dimethyl-L-alanyl-L-valyl)-N^α,9-ethylene-p-phencyclopeptine
• CAS No.: 82837-87-4
• Molecular Formula: C₃₂H₄₃N₅O₅
• Molecular Weight: 577.724

Synonyms:(5S,8R,9R)-5-Benzyl-1,2-dihydro-N^α-(N,N-dimethyl-L-alanyl-L-valyl)-N^α,9-ethylene-p-phencyclopeptine

Chemical Property of (5S,8R,9R)-5-Benzyl-1,2-dihydro-N^α-(N,N-dimethyl-L-alanyl-L-valyl)-N^α,9-ethylene-p-phencyclopeptine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,8R,9R)-5-Benzyl-1,2-dihydro-N^α-(N,N-dimethyl-L-alanyl-L-valyl)-N^α,9-ethylene-p-phencyclopeptine

There total 18 articles about (5S,8R,9R)-5-Benzyl-1,2-dihydro-N^α-(N,N-dimethyl-L-alanyl-L-valyl)-N^α,9-ethylene-p-phencyclopeptine 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:

tyrosamine (51-67-2) → (5S,8R,9R)-5-Benzyl-1,2-dihydro-Nα-(N,N-dimethyl-L-alanyl-L-valyl)-Nα,9-ethylene-p-phencyclopeptine (82837-87-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 92 percent / ethyl acetate / 0.5 h / 25 °C

2: 1. Thallium Ethoxide / 1. ether, 2. DMF, 1.5h, room temperature

3: 0.420 g / NaOH / tetrahydrofuran; H₂O / 1.5 h / 25 °C

4: 0.143 g / dimethylamine borane / acetic acid / 0.5 h / 25 °C

5: 94 percent / triethylamine / tetrahydrofuran; H₂O / 25 °C

6: 94 percent / 1. TFA, 2. DIPEA / 1. 2min. 25 deg C, 2. 30 min, 25 deg C, ethyl acetate

7: 100 percent / pyridine / 4 h / 25 °C

8: 0.05 h / 25 °C

9: pyridine / 21 h / 92 °C / or DIPEA, DMF, 25 deg C, 5d

10: 95 percent / H₂, 10percent HCl / Pd/C / ethanol; H₂O / 2 h / 760 Torr

11: HOBt, DCCl, DIPEA / dimethylformamide / 9 h / 25 °C

With pyridine; hydrogenchloride; sodium hydroxide; hydrogen; thallium (I) ethoxide; dimethylamine borane; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00180a011

Reference yield:

(tert-butoxycarbonyl)-L-phenylalanine N-hydroxysuccinimide ester (3674-06-4,3674-18-8,74124-84-8) → (5S,8R,9R)-5-Benzyl-1,2-dihydro-Nα-(N,N-dimethyl-L-alanyl-L-valyl)-Nα,9-ethylene-p-phencyclopeptine (82837-87-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 98 percent / DIPEA / ethyl acetate / 20 h / 25 °C

2: 1. thallium ethoxide / 1. ether, 25 deg C, 2. a. DMF, 1h, 25 deg C, b. 20h, -15 deg C

3: 1.44 g / NaOH / tetrahydrofuran / 1 h / 25 °C

4: dimethylamine borane / acetic acid / 0.25 h / 25 °C

5: 100 percent / triethylamine / tetrahydrofuran; H₂O / 25 °C

6: 100 percent / pyridine / 4 h / 25 °C

7: 0.05 h / 25 °C

8: pyridine / 21 h / 92 °C / or DIPEA, DMF, 25 deg C, 5d

9: 95 percent / H₂, 10percent HCl / Pd/C / ethanol; H₂O / 2 h / 760 Torr

10: HOBt, DCCl, DIPEA / dimethylformamide / 9 h / 25 °C

With pyridine; hydrogenchloride; sodium hydroxide; hydrogen; thallium (I) ethoxide; dimethylamine borane; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00180a011

Reference yield:

N-t-butoxycarbonyl-tyramine (64318-28-1) → (5S,8R,9R)-5-Benzyl-1,2-dihydro-Nα-(N,N-dimethyl-L-alanyl-L-valyl)-Nα,9-ethylene-p-phencyclopeptine (82837-87-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 1. Thallium Ethoxide / 1. ether, 2. DMF, 1.5h, room temperature

2: 0.420 g / NaOH / tetrahydrofuran; H₂O / 1.5 h / 25 °C

3: 0.143 g / dimethylamine borane / acetic acid / 0.5 h / 25 °C

4: 94 percent / triethylamine / tetrahydrofuran; H₂O / 25 °C

5: 94 percent / 1. TFA, 2. DIPEA / 1. 2min. 25 deg C, 2. 30 min, 25 deg C, ethyl acetate

6: 100 percent / pyridine / 4 h / 25 °C

7: 0.05 h / 25 °C

8: pyridine / 21 h / 92 °C / or DIPEA, DMF, 25 deg C, 5d

9: 95 percent / H₂, 10percent HCl / Pd/C / ethanol; H₂O / 2 h / 760 Torr

10: HOBt, DCCl, DIPEA / dimethylformamide / 9 h / 25 °C

With pyridine; hydrogenchloride; sodium hydroxide; hydrogen; thallium (I) ethoxide; dimethylamine borane; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jo00180a011

upstream raw materials:

N,N-Dimethyl-L-alanyl-L-valine

tyrosamine

N-t-butoxycarbonyl-tyramine

Methyl 3-ethyl>phenoxy>-1-pyrroline-2-carboxylate

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