N-tert-butyloxycarbonyl-(p-sulfomethyl)-L-phenylalanine methyl ester

Base Information

• Chemical Name: N-tert-butyloxycarbonyl-(p-sulfomethyl)-L-phenylalanine methyl ester
• CAS No.: 945245-49-8
• Molecular Formula: C₁₆H₂₃NO₇S
• Molecular Weight: 373.427
• Mol file: 945245-49-8.mol

Synonyms:N-tert-butyloxycarbonyl-(p-sulfomethyl)-L-phenylalanine methyl ester

Chemical Property of N-tert-butyloxycarbonyl-(p-sulfomethyl)-L-phenylalanine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-tert-butyloxycarbonyl-(p-sulfomethyl)-L-phenylalanine methyl ester

There total 5 articles about N-tert-butyloxycarbonyl-(p-sulfomethyl)-L-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: 83.0%

N-tert-butyloxycarbonyl-L-(p-bromomethyl)phenylalanine methyl ester (945245-48-7) → N-tert-butyloxycarbonyl-(p-sulfomethyl)-L-phenylalanine methyl ester (945245-49-8)

Guidance literature:

With water; sodium sulfite; In 1,4-dioxane; for 1h; Heating;

DOI:10.1016/j.tet.2007.03.028

Reference yield:

methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate (112766-18-4) → N-tert-butyloxycarbonyl-(p-sulfomethyl)-L-phenylalanine methyl ester (945245-49-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 58 percent / triphenylphosphine; zinc / bis(triphenylphosphine)nickel bromide / acetonitrile / 1.5 h / 65 °C

2.1: aq. ammonia; hydrogen / Raney nickel / methanol / 3 h / pH 9

3.1: aq. HCl; sodium nitrite / dioxane / 1.5 h / pH 3 / Heating

3.2: 618 mg / aq. NaHCO₃ / dioxane

4.1: 74 percent / triphenylphosphine; N-bromosuccinimide / tetrahydrofuran / 0 - 20 °C

5.1: 83 percent / sodium sulfite; H₂O / dioxane / 1 h / Heating

With hydrogenchloride; ammonium hydroxide; N-Bromosuccinimide; water; hydrogen; triphenylphosphine; sodium sulfite; zinc; sodium nitrite; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; acetonitrile;

DOI:10.1016/j.tet.2007.03.028

Reference yield:

methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-cyanophenyl)propanoate (298693-79-5) → N-tert-butyloxycarbonyl-(p-sulfomethyl)-L-phenylalanine methyl ester (945245-49-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: aq. ammonia; hydrogen / Raney nickel / methanol / 3 h / pH 9

2.1: aq. HCl; sodium nitrite / dioxane / 1.5 h / pH 3 / Heating

2.2: 618 mg / aq. NaHCO₃ / dioxane

3.1: 74 percent / triphenylphosphine; N-bromosuccinimide / tetrahydrofuran / 0 - 20 °C

4.1: 83 percent / sodium sulfite; H₂O / dioxane / 1 h / Heating

With hydrogenchloride; ammonium hydroxide; N-Bromosuccinimide; water; hydrogen; triphenylphosphine; sodium sulfite; sodium nitrite; nickel; In tetrahydrofuran; 1,4-dioxane; methanol;

DOI:10.1016/j.tet.2007.03.028

upstream raw materials:

N-tert-butyloxycarbonyl-L-(p-bromomethyl)phenylalanine methyl ester

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

methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-cyanophenyl)propanoate

N-tert-butyloxycarbonyl-(p-hydroxymethyl)-L-phenylalanine methyl ester

Downstream raw materials:

C₁₅H₂₁NO₇S

N-(fluorenyl-9-methoxycarbonyl)-L-(p-sulfomethyl)phenylalanyl-L-(4-O-benzyl)-aspartic acid α-tert-butyl ester

N-(fluorenyl-9-methoxycarbonyl)-L-(p-sulfomethyl)phenylalanine