Boc-2-Methoxy-L-Phenylalanine

Base Information

• Chemical Name: Boc-2-Methoxy-L-Phenylalanine
• CAS No.: 143415-63-8
• Molecular Formula: C15H21NO5
• Molecular Weight: 295.335
• Mol file: 143415-63-8.mol

Synonyms:L-N-tert-butoxycarbonyl-2-methoxyphenylalanine;

Chemical Property of Boc-2-Methoxy-L-Phenylalanine

Chemical Property:

• Melting Point: 157°C
• PSA: 84.86000
• LogP: 2.60650
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-2-methoxy-L-phenylalanine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Unnatural amino acid was derived from a C-H Activation methodology developed by Jin-Quan Yu and coworkers. The Pd-mediated C-C bond formation can be made in tandem with 2-Methylpyridine (Aldrich 109835).

Technology Process of Boc-2-Methoxy-L-Phenylalanine

There total 7 articles about Boc-2-Methoxy-L-Phenylalanine 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: 77.0%

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) + (S)-2-amino-3-(2-methoxyphenyl)propanoic acid (193546-31-5) → (S)-2-tert-butoxycarbonylamino-3-(2-methoxyphenyl)propionic acid (143415-63-8)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; for 5h; Ambient temperature;

DOI:10.1002/jhet.5570340321

Reference yield:

o-Methoxybenzyl bromide (52289-93-7) → (S)-2-tert-butoxycarbonylamino-3-(2-methoxyphenyl)propionic acid (143415-63-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaOEt / 1.) EtOH, 2.) EtOH, 3 h

2: 94 percent / aq. NaOH / 6 h / Heating

3: 63 percent / Aspergillus acylase I, aq. KOH / 72 h / 40 °C

4: 77 percent / Et₃N / H₂O; dioxane / 5 h / Ambient temperature

With potassium hydroxide; sodium hydroxide; Aspergillus acylase I; sodium ethanolate; triethylamine; In 1,4-dioxane; water;

DOI:10.1002/jhet.5570340321

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + 2-Amino-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-3-(2-methoxy-phenyl)-N-methyl-propionamide → D-N-tert-butoxycarbonyl-2-methoxyphenylalanine (170642-26-9) + (S)-2-tert-butoxycarbonylamino-3-(2-methoxyphenyl)propionic acid (143415-63-8)

Guidance literature:

With sodium hydroxide; Yield given. Multistep reaction. Yields of byproduct given; 1.) H₂₀, reflux, 2.) water, dioxane;

DOI:10.1021/ja9624073

upstream raw materials:

di-tert-butyl dicarbonate

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(R)-2-Amino-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-3-(2-methoxy-phenyl)-N-methyl-propionamide

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Downstream raw materials:

N-tert-butoxycarbonyl-L-2-methoxyphenylalanyl-L-2-methoxyphenylalanine methyl ester

N-tert-butoxycarbonyl-D-2-methoxyphenylalanyl-L-2-methoxyphenylalanine methyl ester

meso-3,6-bis(2-methoxybenzyl)piperazine-2,5-diones

3S,6S-bis(2-methoxybenzyl)piperazine-2,5-dione

Refernces

• 1、 Danthi, Satyavijayan Narasimhan,Hill, Ronald A.. "Synthesis of chirally pure 2,5-disubstituted diketopiperazines derived from trisubstituted phenylalanines". . p. 835 - 844. Retrieved 2007/10/03.