2-(((Benzyloxy)carbonyl)(methyl)amino)propanoic acid

Base Information

• Chemical Name: 2-(((Benzyloxy)carbonyl)(methyl)amino)propanoic acid
• CAS No.: 21691-41-8
• Molecular Formula: C12H15NO4
• Molecular Weight: 237.255
• Hs Code.: 2922509090
• NSC Number: 142289
• Mol file: 21691-41-8.mol

Synonyms:91738-83-9;2-(((Benzyloxy)carbonyl)(methyl)amino)propanoic acid;Z-L-MeAla-OH;Cbz-N-methyl-DL-alanine;2-{[(benzyloxy)carbonyl](methyl)amino}propanoic acid;NSC142289;SCHEMBL381082;2-[methyl(phenylmethoxycarbonyl)amino]propanoic acid;AKOS011920966;NSC-142289;N-((benzyloxy)carbonyl)-N-methylalanine;CS-0457957;FT-0622859;FT-0698824;EN300-139376;2-(((Benzyloxy)carbonyl)(methyl)amino)propanoicacid;(2S)-2-[methyl(phenylmethoxycarbonyl)amino]propanoic acid

Chemical Property of 2-(((Benzyloxy)carbonyl)(methyl)amino)propanoic acid

Chemical Property:

• Vapor Pressure: 9.16E-07mmHg at 25°C
• Melting Point: 54-56ºC
• Refractive Index: 1.545
• Boiling Point: 423 °C at 760 mmHg
• PKA: 4.01±0.10(Predicted)
• Flash Point: 209.6 °C
• PSA: 66.84000
• Density: 1.215 g/cm³
• LogP: 1.72810
• Storage Temp.: 2-8°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 237.10010796
• Heavy Atom Count: 17
• Complexity: 274

Purity/Quality:

98% ^*data from raw suppliers

Z-N-methyl-L-alanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C(=O)O)N(C)C(=O)OCC1=CC=CC=C1

Technology Process of 2-(((Benzyloxy)carbonyl)(methyl)amino)propanoic acid

There total 5 articles about 2-(((Benzyloxy)carbonyl)(methyl)amino)propanoic acid 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: 100.0%

N-Cbz-Ala (1142-20-7) + methyl iodide (74-88-4) → (2S)-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propanoic acid (21691-41-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 7h; Inert atmosphere;

DOI:10.3390/molecules25092153

Reference yield: 94.0%

phenylmethyl (4S)-5-oxo-4-methyl-1,3-oxazolidine-3-carboxylate (37661-60-2) → (2S)-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propanoic acid (21691-41-8)

Guidance literature:

With chloro-trimethyl-silane; sodium cyanoborohydride; In acetonitrile; for 0.25h; Ambient temperature;

DOI:10.1246/cl.1999.299

Reference yield: 75.0%

→ (2S)-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propanoic acid (21691-41-8) + L-N-ethoxycarbonyl-N-methylalanine (79821-70-8)

Guidance literature:

upstream raw materials:

N-Cbz-Ala

methyl iodide

phenylmethyl (4S)-5-oxo-4-methyl-1,3-oxazolidine-3-carboxylate

N-cyclohexyl-cyclohexanamine

Downstream raw materials:

(2S)-{1-[2-(1H-indol-3-yl)-ethyl-carbamoyl]-ethyl}-methyl-carbamic acid benzyl ester

benzyl (1S)-2-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-1-methyl-2-oxoethyl(methyl)carbamate

[2-(2-Hydroxy-3-methyl-phenyl)-1-methyl-2-oxo-ethyl]-methyl-carbamic acid benzyl ester

[2-(2-Amino-3-methyl-phenyl)-1-methyl-2-oxo-ethyl]-methyl-carbamic acid benzyl ester

Refernces

• 1、 Inoue, Kazuya,Nakamura, Noriaki,Ojida, Akio,Uchinomiya, Shohei. "Trimethyl-substituted carbamate as a versatile self-immolative linker for fluorescence detection of enzyme reactions". supporting information. . Retrieved 2020/05/25.
• 2、 Hughes, Andrew B.,Sleebs, Brad E.. "Effective methods for the synthesis of N-methyl β-amino acids from all twenty common α-amino acids using 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones". . p. 2611 - 2637. Retrieved 2007/10/03.