(S)-2-[3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-((S)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-butyrylamino]-3-phenyl-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-[3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-((S)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-butyrylamino]-3-phenyl-propionic acid methyl ester
• CAS No.: 247217-33-0
• Molecular Formula: C₄₀H₄₁N₃O₈
• Molecular Weight: 691.781
• Mol file: 247217-33-0.mol

Synonyms:

Chemical Property of (S)-2-[3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-((S)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-butyrylamino]-3-phenyl-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-((S)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-butyrylamino]-3-phenyl-propionic acid methyl ester

There total 4 articles about (S)-2-[3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-((S)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-butyrylamino]-3-phenyl-propionic acid methyl ester 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: 31.0%

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + fluorenylmethoxycarbonyl-β3-homoaspartate tert-butyl ester (247217-28-3) → Fmoc-homo-β-(L,D)-Asp-L-Phe-OMe + (S)-2-[3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-((S)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-butyrylamino]-3-phenyl-propionic acid methyl ester (247217-33-0)

Guidance literature:

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1002/(SICI)1099-1395(199907)12:7<577::AID-POC159>3.0.CO;2-F

Reference yield:

benzyl-3-amino-4-cyano butyrate → (S)-2-[3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-((S)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-butyrylamino]-3-phenyl-propionic acid methyl ester (247217-33-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Na₂CO₃ / tetrahydrofuran; H₂O / 0 deg C, 30 min., then r.t., 1 h

2: 71 percent / HCl / dioxane; H₂O / 4 h / Heating

3: 12 percent / PyBOP; DIEA / tetrahydrofuran / 2 h / 20 °C

With hydrogenchloride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; water; 1: Esterification / 2: Hydrolysis / 3: Condensation;

DOI:10.1002/(SICI)1099-1395(199907)12:7<577::AID-POC159>3.0.CO;2-F

Reference yield:

3-(N-tert-butyloxycarbonylamino)-4-cyano benzylbutyrate (247217-26-1) → (S)-2-[3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-((S)-1-methoxycarbonyl-2-phenyl-ethylcarbamoyl)-butyrylamino]-3-phenyl-propionic acid methyl ester (247217-33-0)

Guidance literature:

Multi-step reaction with 4 steps

1: TFA / CH₂Cl₂ / 1 h / 20 °C

2: Na₂CO₃ / tetrahydrofuran; H₂O / 0 deg C, 30 min., then r.t., 1 h

3: 71 percent / HCl / dioxane; H₂O / 4 h / Heating

4: 12 percent / PyBOP; DIEA / tetrahydrofuran / 2 h / 20 °C

With hydrogenchloride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; 1: Hydrolysis / 2: Esterification / 3: Hydrolysis / 4: Condensation;

DOI:10.1002/(SICI)1099-1395(199907)12:7<577::AID-POC159>3.0.CO;2-F

upstream raw materials:

methyl (2S)-2-amino-3-phenylpropanoate

fluorenylmethoxycarbonyl-β³-homoaspartate tert-butyl ester

3-(N-tert-butyloxycarbonylamino)-4-cyano benzylbutyrate

3-(N-fluorenylmethoxycarbonylamino)-4-cyano benzylbutyrate