(2S)-2-(methylammonio)propanoate

Base Information

• Chemical Name: (2S)-2-(methylammonio)propanoate
• CAS No.: 3913-67-5
• Molecular Formula: C4H9NO2
• Molecular Weight: 103.121
• Hs Code.: 2922499990
• Mol file: 3913-67-5.mol

Synonyms:N-methylalanine zwitterion;N-methyl-L-alanine zwitterion;CHEBI:58175;(2S)-2-(methylammonio)propanoate;A824422

Chemical Property of (2S)-2-(methylammonio)propanoate

Chemical Property:

• Melting Point: 315-317 °C (decomp)
• Refractive Index: 1.405
• Boiling Point: 190.1 °C at 760 mmHg
• PKA: 2.32±0.10(Predicted)
• Flash Point: 68.8 °C
• PSA: 49.33000
• Density: 1.048 g/cm³
• LogP: 0.06980
• Storage Temp.: Store at RT.
• Solubility.: Aqueous Acid (Slightly), Water (Slightly)
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 103.063328530
• Heavy Atom Count: 7
• Complexity: 66.6

Purity/Quality:

99%+ ^*data from raw suppliers

N-Methyl-L-isoleucine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)[O-])[NH2+]C
• Isomeric SMILES: C[C@@H](C(=O)[O-])[NH2+]C
• Uses: N-Methyl-L-alanine is a reactant used in the preparation of site-specific trastuzumab maytansinoid antibody-drug conjugates with improved therapeutic activity.

Technology Process of (2S)-2-(methylammonio)propanoate

There total 60 articles about (2S)-2-(methylammonio)propanoate 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: 94.0%

(2R,2'R)-N-<2'-(methylamino)propionyl>bornane-10,2-sultam → N-methylalanine (3913-67-5) + N-methyl-D-alanine (29475-64-7)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 0 ℃; Title compound not separated from byproducts;

DOI:10.1002/hlca.19930760113

Reference yield:

odoamide → L-alanin (56-41-7,25191-17-7,18875-37-1) + N-methylalanine (3913-67-5) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) + (2R,3S)-2-hydroxy-3-methylpentanoic acid (488-15-3,51576-04-6,59653-35-9,86540-81-0,86630-77-5,70748-47-9) + N-methyl-D-phenylalanine (56564-52-4)

Guidance literature:

With hydrogenchloride; In water; at 105 ℃; for 12h;

DOI:10.1016/j.tet.2016.07.031

Reference yield:

lagunamide C → L-alanin (56-41-7,25191-17-7,18875-37-1) + N-methylalanine (3913-67-5) + D-allo-isoleucine (1509-34-8,959215-79-3,18875-42-8) + (2R,3S)-2-hydroxy-3-methylpentanoic acid (488-15-3,51576-04-6,59653-35-9,86540-81-0,86630-77-5,70748-47-9) + N-methyl-D-phenylalanine (56564-52-4)

Guidance literature:

With hydrogenchloride; water; at 110 ℃; for 18h;

DOI:10.1016/j.phytochem.2011.08.019

upstream raw materials:

R-(+)-2-bromopropionic acid

methylamine

N-(tert-butoxycarbonyl)-N-methyl-L-alanine

N^α-4-toluenesulfonyl-N^α-methylalanine

Downstream raw materials:

N-methyl-L-alanine methyl ester

N-methyl-D-alanine methyl ester

1,2-dimethyl-3-phenyl-1,2,4,9b-tetrahydro-5-oxa-1-aza-cyclopenta[a]naphthalene

N-{[3-(4-{[4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)phenyl]carbonyl}-N-methyl-L-alanine

Refernces

• 1、 Chen, Baosong,Dai, Huanqin,Han, Junjie,Li, Erwei,Liu, Hongwei,Lyu, Zhitang,Song, Fuhang,Sun, Jingzu,Wang, Hanying,Wang, Tao,Wang, Wenzhao,Zhang, Rui. "Cyclic Tetrapeptides with Synergistic Antifungal Activity from the Fungus Aspergillus westerdijkiae Using LC-MS/MS-Based Molecular Networking". . . Retrieved 2022/02/17.
• 2、 Luo, Danmeng,Putra, Masteria Y.,Ye, Tao,Paul, Valerie J.,Luesch, Hendrik. "Isolation, structure elucidation and biological evaluation of lagunamide D: A new cytotoxic macrocyclic depsipeptide from marine cyanobacteria". . . Retrieved 2019/02/19.