(2S)-1-{[(4-bromophenyl)methoxy]carbonyl}pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S)-1-{[(4-bromophenyl)methoxy]carbonyl}pyrrolidine-2-carboxylic acid
• CAS No.: 144332-75-2
• Molecular Formula: C13H14BrNO4
• Molecular Weight: 328.162
• DSSTox Substance ID: DTXSID901152942
• Mol file: 144332-75-2.mol

Synonyms:144332-75-2;(2S)-1-{[(4-bromophenyl)methoxy]carbonyl}pyrrolidine-2-carboxylic acid;(2S)-1-[(4-Bromophenyl)methoxycarbonyl]pyrrolidine-2-carboxylic acid;DTXSID901152942;EN300-220223;(2S)-1-{[(4-bromophenyl)methoxy]carbonyl}pyrrolidine-2-carboxylicacid;1,2-Pyrrolidinedicarboxylic acid, 1-[(4-bromophenyl)methyl] ester, (S)-

Chemical Property of (2S)-1-{[(4-bromophenyl)methoxy]carbonyl}pyrrolidine-2-carboxylic acid

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 327.01062
• Heavy Atom Count: 19
• Complexity: 342

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)OCC2=CC=C(C=C2)Br)C(=O)O
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)OCC2=CC=C(C=C2)Br)C(=O)O

Technology Process of (2S)-1-{[(4-bromophenyl)methoxy]carbonyl}pyrrolidine-2-carboxylic acid

There total 3 articles about (2S)-1-{[(4-bromophenyl)methoxy]carbonyl}pyrrolidine-2-carboxylic acid 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: 95.0%

(S)-1-(4-bromobenzyl)2-methyl pyrrolidine-1,2-dicarboxylate (144332-74-1) → pBrZ-L-Pro-OH (144332-75-2)

Guidance literature:

With sodium hydroxide; In methanol;

Reference yield:

(4-bromophenyl)methyl 4-nitrophenyl carbonate (38065-38-2) → pBrZ-L-Pro-OH (144332-75-2)

Guidance literature:

Multi-step reaction with 2 steps

1: N-methylmorpholine / tetrahydrofuran

2: 95 percent / 2N NaOH / methanol

With 4-methyl-morpholine; sodium hydroxide; In tetrahydrofuran; methanol;

Reference yield:

4-bromobenzenemethanol (873-75-6) → pBrZ-L-Pro-OH (144332-75-2)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / dichloromethane / 20 h / 20 °C / Inert atmosphere

2: 4-methyl-morpholine / tetrahydrofuran; acetonitrile / 3 h / Reflux; Inert atmosphere

3: lithium hydroxide; water / methanol; tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

With 4-methyl-morpholine; pyridine; water; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1016/j.bmcl.2014.04.002

upstream raw materials:

(S)-1-(4-bromobenzyl)2-methyl pyrrolidine-1,2-dicarboxylate

(4-bromophenyl)methyl 4-nitrophenyl carbonate

4-bromobenzenemethanol

Downstream raw materials:

(S)-(3’-tert-butyl-[1,1’-biphenyl]-4-yl)methyl 2-(((S)-3-amino-1-cyano-3-oxopropyl)carbamoyl)-pyrrolidine-1-carboxylate

(S)-(4’-tert-butyl-[1,1’-biphenyl]-4-yl)methyl 2-(((S)-3-amino-1-cyano-3-oxopropyl)carbamoyl)-pyrrolidine-1-carboxylate

(S)-(3’-fluoro-[1,1’-biphenyl]-4-yl)methyl 2-(((S)-3-amino-1-cyano-3-oxopropyl)carbamoyl)-pyrrolidine-1-carboxylate

(S)-(4’-fluoro-[1,1’-biphenyl]-4-yl)methyl 2-(((S)-3-amino-1-cyano-3-oxopropyl)carbamoyl)-pyrrolidine-1-carboxylate