BOC-L-4-BR-PHE-NITRILE

Base Information

• Chemical Name: BOC-L-4-BR-PHE-NITRILE
• CAS No.: 869570-00-3
• Molecular Formula: C14H17 Br N2 O2
• Molecular Weight: 325.205
• Mol file: 869570-00-3.mol

Synonyms:Carbamicacid, [(1S)-2-(4-bromophenyl)-1-cyanoethyl]-, 1,1-dimethylethyl ester (9CI);(2S)-2-(tert-Butoxycarbonylamino)-3-(4-bromophenyl)propanenitrile

Chemical Property of BOC-L-4-BR-PHE-NITRILE

Chemical Property:

• Boiling Point: 458.6±40.0 °C(Predicted)
• PKA: 9.86±0.46(Predicted)
• PSA: 62.12000
• Density: 1.335
• LogP: 3.79938

Purity/Quality:

98%Min ^*data from raw suppliers

Boc-L-4-Br-Phe-nitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BOC-L-4-BR-PHE-NITRILE

There total 6 articles about BOC-L-4-BR-PHE-NITRILE 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: 88.2%

tert-butyl (S)-(1-amino-3-(4-bromophenyl)-1-oxopropan-2-yl)carbamate (869569-99-3) → tert-butyl (S)-[2-(4-bromophenyl)-1-cyanoethyl]carbamate (869570-00-3)

Guidance literature:

With triethylamine; trifluoroacetic anhydride; In dichloromethane; at 0 - 20 ℃; for 3.5h; Inert atmosphere;

Reference yield:

4-bromo-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalanine (62129-39-9,79561-82-3) → tert-butyl (S)-[2-(4-bromophenyl)-1-cyanoethyl]carbamate (869570-00-3)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C

2: ammonia; methanol / 0.25 h / -50 - 20 °C

3: triethylamine; trifluoroacetic anhydride / dichloromethane / 3.5 h / 0 - 20 °C / Inert atmosphere

With methanol; ammonia; potassium carbonate; triethylamine; trifluoroacetic anhydride; In dichloromethane; N,N-dimethyl-formamide;

Reference yield:

H-p-BrPhe-OH (24250-84-8) → tert-butyl (S)-[2-(4-bromophenyl)-1-cyanoethyl]carbamate (869570-00-3)

Guidance literature:

Multi-step reaction with 4 steps

1: thionyl chloride / Reflux

2: sodium hydrogencarbonate / acetone / 20 °C

3: ammonia; methanol / 0.25 h / -50 - 20 °C

4: triethylamine; trifluoroacetic anhydride / dichloromethane / 3.5 h / 0 - 20 °C / Inert atmosphere

With methanol; thionyl chloride; ammonia; sodium hydrogencarbonate; triethylamine; trifluoroacetic anhydride; In dichloromethane; acetone;

upstream raw materials:

H-p-BrPhe-OH

di-tert-butyl dicarbonate

4-bromo-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalanine

(S)-3-(4-Bromo-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester

Downstream raw materials:

(S)-D₆-1-amino-N-(1-cyano-2-(4'-((4-methyl-piperazin-1-yl)methyl)biphenyl-4-yl)ethyl)cyclohexanecarboxamide

(R)-1-amino-N-(1-cyano-2-(4'-((4-propylpiperazin-1-yl)methyl)biphenyl-4-yl)ethyl)cyclohexanecarboxamide

(R)-1-amino-N-(1-cyano-2-(4'-((4-cyclopropyl-piperazin-1-yl)methyl)biphenyl-4-yl)ethyl)cyclohexanecarboxamide

(R)-1-amino-N-(1-cyano-2-(4'-((4-(cyanomethyl)piperazin-1-yl)methyl)biphenyl-4-yl)ethyl)cyclohexanecarboxamide

Refernces

• 1、 -. "PEPTIDYL NITRIL COMPOUNDS AS DIPEPTIDYL PEPTIDASE I INHIBITORS". . . Retrieved 2015/03/28.
• 2、 -. "N-SUBSTITUTED 3,3'-(BIPHENYL-4,4'-DIYL)BIS-2-AMINOPROPANENITRILES AS DPPI INHIBITORS". . . Retrieved 2015/03/28.