(R)-2-{4-chloro-N-{[(1s,3r)-3-cyano-3-methylcyclobutyl]methyl}-phenylsulfonamido}-5,5,5-trifluoropentanamide

Base Information

• Chemical Name: (R)-2-{4-chloro-N-{[(1s,3r)-3-cyano-3-methylcyclobutyl]methyl}-phenylsulfonamido}-5,5,5-trifluoropentanamide
• CAS No.: 1372118-37-0
• Molecular Formula: C₁₈H₂₁ClF₃N₃O₃S
• Molecular Weight: 451.897
• Mol file: 1372118-37-0.mol

Synonyms:(R)-2-{4-chloro-N-{[(1s,3r)-3-cyano-3-methylcyclobutyl]methyl}-phenylsulfonamido}-5,5,5-trifluoropentanamide

Chemical Property of (R)-2-{4-chloro-N-{[(1s,3r)-3-cyano-3-methylcyclobutyl]methyl}-phenylsulfonamido}-5,5,5-trifluoropentanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-{4-chloro-N-{[(1s,3r)-3-cyano-3-methylcyclobutyl]methyl}-phenylsulfonamido}-5,5,5-trifluoropentanamide

There total 3 articles about (R)-2-{4-chloro-N-{[(1s,3r)-3-cyano-3-methylcyclobutyl]methyl}-phenylsulfonamido}-5,5,5-trifluoropentanamide 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: 1.3%

(R)-2-(4-chlorophenylsulfonamido)-5,5,5-trifluoropentanamide (1146699-67-3) + 3-(hydroxymethyl)-1-methylcyclobutanecarbonitrile (1370705-52-4) → (R)-2-{4-chloro-N-{[(1s,3r)-3-cyano-3-methylcyclobutyl]methyl}-phenylsulfonamido}-5,5,5-trifluoropentanamide (1372118-37-0) + (R)-2-{4-chloro-N-{[(1r,3s)-3-cyano-3-methylcyclobutyl]methyl}-phenylsulfonamido}-5,5,5-trifluoropentanamide (1372118-38-1)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 23 ℃;

DOI:10.1021/jm300094u

Reference yield:

3-methylenecyclobutanecarbonitrile (15760-35-7) → (R)-2-{4-chloro-N-{[(1s,3r)-3-cyano-3-methylcyclobutyl]methyl}-phenylsulfonamido}-5,5,5-trifluoropentanamide (1372118-37-0) + (R)-2-{4-chloro-N-{[(1r,3s)-3-cyano-3-methylcyclobutyl]methyl}-phenylsulfonamido}-5,5,5-trifluoropentanamide (1372118-38-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 16 h / -78 - 23 °C

2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 2.17 h

2.2: 12 h / 20 °C

3.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 23 °C

With 9-borabicyclo[3.3.1]nonane dimer; di-isopropyl azodicarboxylate; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; 3.1: Mitsunobu reaction;

DOI:10.1021/jm300094u

Reference yield:

1-methyl-3-methylenecyclobutane-1-carbonitrile (32082-16-9) → (R)-2-{4-chloro-N-{[(1s,3r)-3-cyano-3-methylcyclobutyl]methyl}-phenylsulfonamido}-5,5,5-trifluoropentanamide (1372118-37-0) + (R)-2-{4-chloro-N-{[(1r,3s)-3-cyano-3-methylcyclobutyl]methyl}-phenylsulfonamido}-5,5,5-trifluoropentanamide (1372118-38-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 2.17 h

1.2: 12 h / 20 °C

2.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 23 °C

With 9-borabicyclo[3.3.1]nonane dimer; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; 2.1: Mitsunobu reaction;

DOI:10.1021/jm300094u

upstream raw materials:

(R)-2-(4-chlorophenylsulfonamido)-5,5,5-trifluoropentanamide

3-(hydroxymethyl)-1-methylcyclobutanecarbonitrile

3-methylenecyclobutanecarbonitrile

1-methyl-3-methylenecyclobutane-1-carbonitrile