N-tert-butoxycarbonyl-cis-3-(p-nitrobenzoyloxy)-L-proline methyl ester

Base Information

• Chemical Name: N-tert-butoxycarbonyl-cis-3-(p-nitrobenzoyloxy)-L-proline methyl ester
• CAS No.: 361367-98-8
• Molecular Formula: C₁₈H₂₂N₂O₈
• Molecular Weight: 394.381
• Mol file: 361367-98-8.mol

Synonyms:N-tert-butoxycarbonyl-cis-3-(p-nitrobenzoyloxy)-L-proline methyl ester

Chemical Property of N-tert-butoxycarbonyl-cis-3-(p-nitrobenzoyloxy)-L-proline methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-tert-butoxycarbonyl-cis-3-(p-nitrobenzoyloxy)-L-proline methyl ester

There total 5 articles about N-tert-butoxycarbonyl-cis-3-(p-nitrobenzoyloxy)-L-proline 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: 90.0%

(2S,3S)-1-tert-butyl-2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate (184046-78-4) + 4-nitro-benzoic acid (62-23-7) → N-tert-butoxycarbonyl-cis-3-(p-nitrobenzoyloxy)-L-proline methyl ester (361367-98-8)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1021/ol0161054

Reference yield:

trans-3-hydroxy-L-proline (4298-08-2) → N-tert-butoxycarbonyl-cis-3-(p-nitrobenzoyloxy)-L-proline methyl ester (361367-98-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / aq. NaOH / tetrahydrofuran

2: diethyl ether

3: PPh₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 3 h

With sodium hydroxide; di-isopropyl azodicarboxylate; In tetrahydrofuran; diethyl ether; 3: Mitsunobu reaction;

DOI:10.1021/ja054674r

Reference yield:

(2S,3S)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (187039-57-2,335280-19-8) → N-tert-butoxycarbonyl-cis-3-(p-nitrobenzoyloxy)-L-proline methyl ester (361367-98-8)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether

2: PPh₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 3 h

With di-isopropyl azodicarboxylate; In tetrahydrofuran; diethyl ether; 2: Mitsunobu reaction;

DOI:10.1021/ja054674r

upstream raw materials:

(2S,3S)-1-tert-butyl-2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate

4-nitro-benzoic acid

di-tert-butyl dicarbonate

trans-3-hydroxy-L-proline

Downstream raw materials:

2-benzyl 1-(tert-butyl) (2R,3S)-3-fluoropyrrolidine-1,2-dicarboxylate

(2R,3S)-1-tert-butoxycarbonyl-3-fluoro-pyrrolidine-2-carboxylic acid

2-benzyl 1-(tert-butyl)(2S,3R)-3-hydroxypyrrolidine-1,2-dicarboxylate

N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester