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

Base Information

• Chemical Name: (S)-(3’-tert-butyl-[1,1’-biphenyl]-4-yl)methyl 2-(((S)-3-amino-1-cyano-3-oxopropyl)carbamoyl)-pyrrolidine-1-carboxylate
• CAS No.: 1609689-87-3
• Molecular Formula: C₂₇H₃₂N₄O₄
• Molecular Weight: 476.575
• Mol file: 1609689-87-3.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (S)-(3’-tert-butyl-[1,1’-biphenyl]-4-yl)methyl 2-(((S)-3-amino-1-cyano-3-oxopropyl)carbamoyl)-pyrrolidine-1-carboxylate 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:

(S)-4-bromobenzyl 2-(((S)-3-amino-1-cyano-3-oxopropyl)carbamoyl)pyrrolidine-1-carboxylate (1609689-78-2) + 3-tert-butylphenylboronic acid (560132-24-3) → (S)-(3’-tert-butyl-[1,1’-biphenyl]-4-yl)methyl 2-(((S)-3-amino-1-cyano-3-oxopropyl)carbamoyl)-pyrrolidine-1-carboxylate (1609689-87-3)

Guidance literature:

With sodium carbonate; In water; N,N-dimethyl-formamide; at 60 ℃;

DOI:10.1016/j.bmcl.2014.04.002

Reference yield:

(S)-1-(4-bromobenzyl)2-methyl pyrrolidine-1,2-dicarboxylate (144332-74-1) → (S)-(3’-tert-butyl-[1,1’-biphenyl]-4-yl)methyl 2-(((S)-3-amino-1-cyano-3-oxopropyl)carbamoyl)-pyrrolidine-1-carboxylate (1609689-87-3)

Guidance literature:

Multi-step reaction with 6 steps

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

2.1: 4-methyl-morpholine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

3.1: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: lithium hydroxide; water / 4 h / 20 °C / Inert atmosphere

5.1: 4-methyl-morpholine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; ammonium chloride / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

6.1: sodium carbonate / N,N-dimethyl-formamide; water / 60 °C

With 4-methyl-morpholine; 1,3,5-trichloro-2,4,6-triazine; water; sodium carbonate; ammonium chloride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; lithium hydroxide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2014.04.002

Reference yield:

(S)-4-bromobenzyl 2-(((S)-3-(benzyloxy)-1-cyano-3-oxopropyl)carbamoyl)pyrrolidine-1-carboxylate (1609689-75-9) → (S)-(3’-tert-butyl-[1,1’-biphenyl]-4-yl)methyl 2-(((S)-3-amino-1-cyano-3-oxopropyl)carbamoyl)-pyrrolidine-1-carboxylate (1609689-87-3)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium hydroxide; water / 4 h / 20 °C / Inert atmosphere

2: 4-methyl-morpholine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; ammonium chloride / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

3: sodium carbonate / N,N-dimethyl-formamide; water / 60 °C

With 4-methyl-morpholine; water; sodium carbonate; ammonium chloride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; lithium hydroxide; In water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2014.04.002

upstream raw materials:

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

(S)-4-bromobenzyl 2-(((S)-3-(benzyloxy)-1-cyano-3-oxopropyl)carbamoyl)pyrrolidine-1-carboxylate

(4-bromophenyl)methyl 4-nitrophenyl carbonate

(S)-4-bromobenzyl 2-(((S)-3-amino-1-cyano-3-oxopropyl)carbamoyl)pyrrolidine-1-carboxylate