(3R,4S)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester

Base Information

• Chemical Name: (3R,4S)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester
• CAS No.: 1345261-66-6
• Molecular Formula: C₃₁H₂₇F₅N₂O₆
• Molecular Weight: 618.557
• Mol file: 1345261-66-6.mol

Synonyms:(3R,4S)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester

Chemical Property of (3R,4S)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester

There total 6 articles about (3R,4S)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl 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: 60.0%

pentafluorophenyl trifloroacetate (14533-84-7) + (3R,4S)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxycarbonylpyrrolidine (346610-79-5) → (3R,4S)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester (1345261-66-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/j.bmcl.2011.08.079

Reference yield:

C20H28N2O4 → (3R,4S)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester (1345261-66-6)

Guidance literature:

Multi-step reaction with 5 steps

1: hydrogenchloride / ethyl acetate / 0 °C

2: water; lithium hydroxide / tetrahydrofuran; methanol / 0 °C

3: palladium on activated charcoal; hydrogen / ethanol / 20 °C

4: sodium hydrogencarbonate / water; acetone

5: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 °C

With hydrogenchloride; palladium on activated charcoal; water; hydrogen; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone;

DOI:10.1016/j.bmcl.2011.08.079

Reference yield:

C12H19NO5 → (3R,4S)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester (1345261-66-6)

Guidance literature:

Multi-step reaction with 6 steps

1: acetic acid / ethanol / 20 °C

2: hydrogenchloride / ethyl acetate / 0 °C

3: water; lithium hydroxide / tetrahydrofuran; methanol / 0 °C

4: palladium on activated charcoal; hydrogen / ethanol / 20 °C

5: sodium hydrogencarbonate / water; acetone

6: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 °C

With hydrogenchloride; palladium on activated charcoal; water; hydrogen; sodium hydrogencarbonate; acetic acid; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone;

DOI:10.1016/j.bmcl.2011.08.079

upstream raw materials:

pentafluorophenyl trifloroacetate

(3R,4S)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxycarbonylpyrrolidine

4-amino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester

(3R,4S)-1-(N-tert-butoxycarbonyl)-3-[(1'S)-phenylethylamino]pyrrolidine-4-carboxylic acid ethyl ester hydrochloride