[(2R)-3,6-dioxopiperazin-2-yl]methyl (2R,4R)-2-benzyl-2-[[(2S)-3-(2-chloro-3-hydroxy-4-methoxyphenyl)-2-(methylamino)propanoyl]-methylamino]-5-(4-hydroxyphenyl)-3-oxo-4-[[(E)-3-[2-[(E)-pent-2-enyl]phenyl]prop-2-enoyl]amino]pentanoate

Base Information

• Chemical Name: [(2R)-3,6-dioxopiperazin-2-yl]methyl (2R,4R)-2-benzyl-2-[[(2S)-3-(2-chloro-3-hydroxy-4-methoxyphenyl)-2-(methylamino)propanoyl]-methylamino]-5-(4-hydroxyphenyl)-3-oxo-4-[[(E)-3-[2-[(E)-pent-2-enyl]phenyl]prop-2-enoyl]amino]pentanoate
• CAS No.: 147317-36-0
• Molecular Formula: C₄₉H₅₄ClN₅O₁₀
• Molecular Weight: 908.448
• Wikidata: Q77279162
• Metabolomics Workbench ID: 115749
• Mol file: 147317-36-0.mol

Synonyms:[(2R)-3,6-dioxopiperazin-2-yl]methyl (2R,4R)-2-benzyl-2-[[(2S)-3-(2-chloro-3-hydroxy-4-methoxyphenyl)-2-(methylamino)propanoyl]-methylamino]-5-(4-hydroxyphenyl)-3-oxo-4-[[(E)-3-[2-[(E)-pent-2-enyl]phenyl]prop-2-enoyl]amino]pentanoate;[(2R)-3,6-Dioxopiperazin-2-yl]methyl (2S)-2-[[(2S)-3-(2-chloro-3-hydroxy-4-methoxyphenyl)-2-[[(2R)-3-(4-hydroxyphenyl)-2-[[(E)-3-[2-[(Z)-pent-1-enyl]phenyl]prop-2-enoyl]amino]propanoyl]-methylamino]propanoyl]-methylamino]-3-phenylpropanoate;L-Phenylalanine, N-(2-chloro-3-hydroxy-N,O-dimethyl-N-(N-(1-oxo-3-(2-(1-pentenyl)phenyl)-2-propenyl)-D-tyrosyl)tyrosyl)-N-methyl-, (3,6-dioxo-2-piperazinyl)methyl ester, (R-(E,Z))-

Chemical Property of [(2R)-3,6-dioxopiperazin-2-yl]methyl (2R,4R)-2-benzyl-2-[[(2S)-3-(2-chloro-3-hydroxy-4-methoxyphenyl)-2-(methylamino)propanoyl]-methylamino]-5-(4-hydroxyphenyl)-3-oxo-4-[[(E)-3-[2-[(E)-pent-2-enyl]phenyl]prop-2-enoyl]amino]pentanoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1124.3°C at 760 mmHg
• Flash Point: 633.7°C
• PSA: 223.17000
• Density: 1.284g/cm³
• LogP: 5.78970
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 22
• Exact Mass: 907.3559206
• Heavy Atom Count: 65
• Complexity: 1670

Purity/Quality:

PEPTICINNAMIN E 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC1=CC=CC=C1C=CC(=O)NC(CC2=CC=C(C=C2)O)C(=O)C(CC3=CC=CC=C3)(C(=O)OCC4C(=O)NCC(=O)N4)N(C)C(=O)C(CC5=C(C(=C(C=C5)OC)O)Cl)NC
• Isomeric SMILES: CC/C=C/CC1=CC=CC=C1/C=C/C(=O)N[C@H](CC2=CC=C(C=C2)O)C(=O)[C@](CC3=CC=CC=C3)(C(=O)OC[C@@H]4C(=O)NCC(=O)N4)N(C)C(=O)[C@H](CC5=C(C(=C(C=C5)OC)O)Cl)NC
• Uses: Pepticinnamin E is a farnesyl‐transferase inhibitor.

Technology Process of [(2R)-3,6-dioxopiperazin-2-yl]methyl (2R,4R)-2-benzyl-2-[[(2S)-3-(2-chloro-3-hydroxy-4-methoxyphenyl)-2-(methylamino)propanoyl]-methylamino]-5-(4-hydroxyphenyl)-3-oxo-4-[[(E)-3-[2-[(E)-pent-2-enyl]phenyl]prop-2-enoyl]amino]pentanoate

There total 50 articles about [(2R)-3,6-dioxopiperazin-2-yl]methyl (2R,4R)-2-benzyl-2-[[(2S)-3-(2-chloro-3-hydroxy-4-methoxyphenyl)-2-(methylamino)propanoyl]-methylamino]-5-(4-hydroxyphenyl)-3-oxo-4-[[(E)-3-[2-[(E)-pent-2-enyl]phenyl]prop-2-enoyl]amino]pentanoate 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:

2-chloro-3-hydroxy-4-methoxybenzaldehyde (37687-57-3) → pepticinnamin E (147317-36-0)

Guidance literature:

Multi-step reaction with 15 steps

1: 93 percent / K₂CO₃ / dimethylformamide / 48 h / Ambient temperature

2: 99 percent / NaBH₄ / tetrahydrofuran; methanol / 5 h / 40 °C

3: 85 percent / PPh₃, CBr₄ / diethyl ether / 20 h / Ambient temperature

4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 5 h

5: HCl, H₂O / tetrahydrofuran / 16 h / Ambient temperature

6: 88 percent / NEt₃ / methanol / 15 h / Ambient temperature

7: 99 percent / LiOH, H₂O / tetrahydrofuran / 3 h / Ambient temperature

8: 96 percent / NaH / tetrahydrofuran / 16 h / 0 °C

9: 81 percent / hydroxyazobenzotriazole, NEt₃, EDC / dimethylformamide / 1.) 0 deg C, 15 min, 2.) r.t., 14 h

10: HCl / diethyl ether / 1.5 h / Ambient temperature

11: 77 percent / EDC, hydroxyazobenzotriazole, NEt₃ / dimethylformamide / 16 h / 0 °C

12: 89 percent / morpholine / Pd(PPh₃)4 / CH₂Cl₂ / 4 h / Ambient temperature

13: 53 percent / DEAD, PPh₃ / dimethylformamide / 24 h / Ambient temperature

14: H₂, AcOH / Pd/C / ethyl acetate; ethanol / 18 h

15: NEt₃ / dimethylformamide / 16 h / Ambient temperature

With morpholine; hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; n-butyllithium; carbon tetrabromide; hydroxyazobenzotriazole; water; hydrogen; sodium hydride; potassium carbonate; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/(sici)1521-3765(19990104)5:1<227::aid-chem227>3.3.co;2-o

Reference yield:

2-chloro-3-hydroxy-4-methoxybenzaldehyde (37687-57-3) → epi-pepticinnamin E (147317-36-0)

Guidance literature:

Multi-step reaction with 15 steps

1: 93 percent / K₂CO₃ / dimethylformamide / 48 h / Ambient temperature

2: 99 percent / NaBH₄ / tetrahydrofuran; methanol / 5 h / 40 °C

3: 85 percent / PPh₃, CBr₄ / diethyl ether / 20 h / Ambient temperature

4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 5 h

5: HCl, H₂O / tetrahydrofuran / 16 h / Ambient temperature

6: 88 percent / NEt₃ / methanol / 15 h / Ambient temperature

7: 99 percent / LiOH, H₂O / tetrahydrofuran / 3 h / Ambient temperature

8: 96 percent / NaH / tetrahydrofuran / 16 h / 0 °C

9: 81 percent / hydroxyazobenzotriazole, NEt₃, EDC / dimethylformamide / 1.) 0 deg C, 15 min, 2.) r.t., 14 h

10: HCl / diethyl ether / 1.5 h / Ambient temperature

11: 75 percent / EDC, hydroxyazobenzotriazole, NEt₃ / dimethylformamide / 16 h / 0 °C

12: 88 percent / morpholine / Pd(PPh₃)4 / CH₂Cl₂ / 4 h / Ambient temperature

13: 55 percent / DEAD, PPh₃ / dimethylformamide / 24 h / Ambient temperature

14: H₂, AcOH / Pd/C / ethyl acetate; ethanol / 18 h

15: hydroxyazobenzotriazole, NEt₃, EDC / dimethylformamide / 16 h / Ambient temperature

With morpholine; hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; n-butyllithium; carbon tetrabromide; hydroxyazobenzotriazole; water; hydrogen; sodium hydride; potassium carbonate; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/(sici)1521-3765(19990104)5:1<227::aid-chem227>3.3.co;2-o

Reference yield:

3-benzyloxy-2-chloro-4-methoxy-benzaldehyde (53713-77-2) → pepticinnamin E (147317-36-0)

Guidance literature:

Multi-step reaction with 14 steps

1: 99 percent / NaBH₄ / tetrahydrofuran; methanol / 5 h / 40 °C

2: 85 percent / PPh₃, CBr₄ / diethyl ether / 20 h / Ambient temperature

3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 5 h

4: HCl, H₂O / tetrahydrofuran / 16 h / Ambient temperature

5: 88 percent / NEt₃ / methanol / 15 h / Ambient temperature

6: 99 percent / LiOH, H₂O / tetrahydrofuran / 3 h / Ambient temperature

7: 96 percent / NaH / tetrahydrofuran / 16 h / 0 °C

8: 81 percent / hydroxyazobenzotriazole, NEt₃, EDC / dimethylformamide / 1.) 0 deg C, 15 min, 2.) r.t., 14 h

9: HCl / diethyl ether / 1.5 h / Ambient temperature

10: 77 percent / EDC, hydroxyazobenzotriazole, NEt₃ / dimethylformamide / 16 h / 0 °C

11: 89 percent / morpholine / Pd(PPh₃)4 / CH₂Cl₂ / 4 h / Ambient temperature

12: 53 percent / DEAD, PPh₃ / dimethylformamide / 24 h / Ambient temperature

13: H₂, AcOH / Pd/C / ethyl acetate; ethanol / 18 h

14: NEt₃ / dimethylformamide / 16 h / Ambient temperature

With morpholine; hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; n-butyllithium; carbon tetrabromide; hydroxyazobenzotriazole; water; hydrogen; sodium hydride; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/(sici)1521-3765(19990104)5:1<227::aid-chem227>3.3.co;2-o

upstream raw materials:

3-(2-(1-Z-pentenyl)phenyl)-E-acrylic acid hydroxyazo benzotriazolyl ester

methyl o-formylbenzoate

3-benzyloxy-2-chloro-4-methoxy-benzaldehyde

2-chloro-3-hydroxy-4-methoxybenzaldehyde