methyl 2S-2-N-benzylamino-4,4-dimethoxybutanoate

Base Information

• Chemical Name: methyl 2S-2-N-benzylamino-4,4-dimethoxybutanoate
• CAS No.: 159111-89-4
• Molecular Formula: C₁₄H₂₁NO₄
• Molecular Weight: 267.325
• Mol file: 159111-89-4.mol

Synonyms:methyl 2S-2-N-benzylamino-4,4-dimethoxybutanoate

Chemical Property of methyl 2S-2-N-benzylamino-4,4-dimethoxybutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2S-2-N-benzylamino-4,4-dimethoxybutanoate

There total 6 articles about methyl 2S-2-N-benzylamino-4,4-dimethoxybutanoate 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: 71.0%

benzyl bromide (100-39-0) + methyl 2S-2-amino-4,4-dimethoxybutanoate (159111-88-3) → methyl 2S-2-N-benzylamino-4,4-dimethoxybutanoate (159111-89-4)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/S0040-4039(00)78176-7

Reference yield:

benzyl bromide (100-39-0) → methyl 2S-2-N-benzylamino-4,4-dimethoxybutanoate (159111-89-4)

Guidance literature:

With triethylamine; In N-methyl-acetamide; ethyl acetate;

Reference yield:

(S)-2-benzyloxycarbonylamino-succinic acid 1-methyl ester (4668-42-2) → methyl 2S-2-N-benzylamino-4,4-dimethoxybutanoate (159111-89-4)

Guidance literature:

Multi-step reaction with 5 steps

1: SOCl₂ / Ambient temperature

2: n-Bu₃SnH, (Ph₃P)4Pd / tetrahydrofuran / Ambient temperature

3: p-TSA / methanol / Heating

4: 84 percent / H₂ / 5percent Pd/C / methanol / 2068.6 Torr / Ambient temperature

5: 71 percent / Et₃N / dimethylformamide / Ambient temperature

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; hydrogen; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)78176-7

upstream raw materials:

benzyl bromide

methyl 2S-2-amino-4,4-dimethoxybutanoate

(S)-2-benzyloxycarbonylamino-succinic acid 1-methyl ester

methyl (S)-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoate

Refernces

• 1、 Omstein, Paul L.,Melikian, Anita,Martinelli, Michael J.. "Intramolecular Diels-Alder Route To 6-octadecahydroisoquinoline-3-Carboxylates: Intermediates For The Synthesis Of Conformationally Constrained Excitatory Amino Acid Antagonists". . p. 5759 - 5762. Retrieved 2007/10/02.