(2S,3aS,6R,7aS)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-6-(2,2,2-trifluoro-acetoxy)-octahydro-indole-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3aS,6R,7aS)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-6-(2,2,2-trifluoro-acetoxy)-octahydro-indole-2-carboxylic acid methyl ester
• CAS No.: 444911-13-1
• Molecular Formula: C₂₆H₃₃F₃N₂O₇
• Molecular Weight: 542.552
• Mol file: 444911-13-1.mol

Synonyms:

Chemical Property of (2S,3aS,6R,7aS)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-6-(2,2,2-trifluoro-acetoxy)-octahydro-indole-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3aS,6R,7aS)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-6-(2,2,2-trifluoro-acetoxy)-octahydro-indole-2-carboxylic acid methyl ester

There total 1 articles about (2S,3aS,6R,7aS)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-6-(2,2,2-trifluoro-acetoxy)-octahydro-indole-2-carboxylic 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:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + trifluoroacetic acid (76-05-1) + methyl (2S,3aS,6R,7aS)-1-tert-butoxycarbonyl-6-hydroxy-octahydroindole-2-carboxylate (313952-04-4) → (2S,3aS,6R,7aS)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-6-hydroxy-octahydro-indole-2-carboxylic acid methyl ester + (2S,3aS,6R,7aS)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-6-(2,2,2-trifluoro-acetoxy)-octahydro-indole-2-carboxylic acid methyl ester (444911-13-1)

Guidance literature:

trifluoroacetic acid; methyl (2S,3aS,6R,7aS)-1-tert-butoxycarbonyl-6-hydroxy-octahydroindole-2-carboxylate; In dichloromethane; at 0 ℃; for 2h;

N-tert-butoxycarbonyl-L-phenylalanine; With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In dichloromethane; at 0 - 20 ℃; for 22.5h; Further stages.;

DOI:10.1021/jo025709y

Reference yield:

(2S,3aS,6R,7aS)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-6-(2,2,2-trifluoro-acetoxy)-octahydro-indole-2-carboxylic acid methyl ester (444911-13-1) → microcin SF608

Guidance literature:

Multi-step reaction with 5 steps

1.1: TFA / CH₂Cl₂ / 0.83 h / 0 °C

1.2: 120 mg / PyBOP; 4-methylmorpholine / CH₂Cl₂ / 22 h / 20 °C

2.1: 86 percent / 0.1 mol/l LiOH / tetrahydrofuran / 20 h / 20 °C

3.1: 77 percent / PyBOP; 4-methylmorpholine / dimethylformamide / 22.5 h / 0 - 20 °C

4.1: 6 mol/l HCl / acetonitrile / 6 h / 20 °C

5.1: 99 percent / H₂ / 10 percent Pd/C / ethyl acetate; methanol / 24 h / atmospheric pressure

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; trifluoroacetic acid; 10 percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo025709y

Reference yield:

(S)-2-acetyloxy-3-(4-benzyloxyphenyl)propionic acid (267228-34-2) + (2S,3aS,6R,7aS)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-6-(2,2,2-trifluoro-acetoxy)-octahydro-indole-2-carboxylic acid methyl ester (444911-13-1) → (2S,3aS,6R,7aS)-1-{(S)-2-[(S)-2-Acetoxy-3-(4-benzyloxy-phenyl)-propionylamino]-3-phenyl-propionyl}-6-hydroxy-octahydro-indole-2-carboxylic acid methyl ester (444911-09-5) + (2S,3aS,6R,7aS)-1-{(S)-2-[(S)-2-Acetoxy-3-(4-benzyloxy-phenyl)-propionylamino]-3-phenyl-propionyl}-6-(2,2,2-trifluoro-acetoxy)-octahydro-indole-2-carboxylic acid methyl ester

Guidance literature:

(2S,3aS,6R,7aS)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-6-(2,2,2-trifluoro-acetoxy)-octahydro-indole-2-carboxylic acid methyl ester; With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.833333h;

(S)-2-acetyloxy-3-(4-benzyloxyphenyl)propionic acid; With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In dichloromethane; at 20 ℃; for 22h; Further stages.;

DOI:10.1021/jo025709y

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

trifluoroacetic acid

methyl (2S,3aS,6R,7aS)-1-tert-butoxycarbonyl-6-hydroxy-octahydroindole-2-carboxylate

Downstream raw materials:

(2S,3aS,6R,7aS)-1-{(S)-2-[(S)-2-Acetoxy-3-(4-benzyloxy-phenyl)-propionylamino]-3-phenyl-propionyl}-6-hydroxy-octahydro-indole-2-carboxylic acid methyl ester

C₄₉H₆₆N₆O₁₀