Boc-4-(1'-cyclohexenyl)phenylalanine methyl ester

Base Information

• Chemical Name: Boc-4-(1'-cyclohexenyl)phenylalanine methyl ester
• CAS No.: 1396174-20-1
• Molecular Formula: C₂₁H₂₉NO₄
• Molecular Weight: 359.466
• Mol file: 1396174-20-1.mol

Synonyms:Boc-4-(1'-cyclohexenyl)phenylalanine methyl ester

Chemical Property of Boc-4-(1'-cyclohexenyl)phenylalanine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Boc-4-(1'-cyclohexenyl)phenylalanine methyl ester

There total 4 articles about Boc-4-(1'-cyclohexenyl)phenylalanine 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: 93.0%

methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate (112766-18-4) + 2-(cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (141091-37-4) → Boc-4-(1'-cyclohexenyl)phenylalanine methyl ester (1396174-20-1)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In N,N-dimethyl-formamide; toluene; at 90 ℃; Inert atmosphere;

DOI:10.1016/j.bmc.2012.07.010

Reference yield:

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → Boc-4-(1'-cyclohexenyl)phenylalanine methyl ester (1396174-20-1)

Guidance literature:

Multi-step reaction with 4 steps

1: thionyl chloride / 4 h / Reflux

2: triethylamine / methanol / 20 °C / Cooling with ice; Inert atmosphere

3: pyridine / dichloromethane / 0.5 h / -15 °C / Inert atmosphere

4: potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate / toluene; N,N-dimethyl-formamide / 90 °C / Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; pyridine; potassium phosphate; thionyl chloride; palladium diacetate; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 4: |Suzuki Coupling;

DOI:10.1016/j.bmc.2012.07.010

Reference yield:

L-Tyr-OMe (1080-06-4) → Boc-4-(1'-cyclohexenyl)phenylalanine methyl ester (1396174-20-1)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / methanol / 20 °C / Cooling with ice; Inert atmosphere

2: pyridine / dichloromethane / 0.5 h / -15 °C / Inert atmosphere

3: potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate / toluene; N,N-dimethyl-formamide / 90 °C / Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; pyridine; potassium phosphate; palladium diacetate; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 3: |Suzuki Coupling;

DOI:10.1016/j.bmc.2012.07.010

upstream raw materials:

L-tyrosine

L-Tyr-OMe

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate