Methyl 2-([(benzyloxy)carbonyl](methyl)amino)acetate

Base Information

• Chemical Name: Methyl 2-([(benzyloxy)carbonyl](methyl)amino)acetate
• CAS No.: 100391-80-8
• Molecular Formula: C12H15NO4
• Molecular Weight: 237.255
• DSSTox Substance ID: DTXSID801202586
• Mol file: 100391-80-8.mol

Synonyms:100391-80-8;Methyl 2-([(benzyloxy)carbonyl](methyl)amino)acetate;DTXSID801202586;AKOS009023395;N-Methyl-N-[(phenylmethoxy)carbonyl]glycine methyl ester

Chemical Property of Methyl 2-([(benzyloxy)carbonyl](methyl)amino)acetate

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 237.10010796
• Heavy Atom Count: 17
• Complexity: 261

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl 2-([(benzyloxy)carbonyl](methyl)amino)acetate

There total 2 articles about Methyl 2-([(benzyloxy)carbonyl](methyl)amino)acetate 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-methylglycine methyl ester hydrochloride (13515-93-0) + benzyl chloroformate (501-53-1,94274-21-2) → Cbz-Sar-OMe (100391-80-8)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; water; at 0 - 20 ℃; for 16h;

DOI:10.1002/adsc.202100964

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + N-(Benzyloxycarbonyl)sarcosine (39608-31-6) → Cbz-Sar-OMe (100391-80-8)

Guidance literature:

With diethyl ether; ethanol;

DOI:10.1002/hlca.19590420523

Reference yield: 65.0%

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2,45842-10-2,126517-51-9,25657-03-8,26933-82-4,54637-06-8,64104-42-3) + Cbz-Sar-OMe (100391-80-8) → methyl N-(benzyloxycarbonyl)-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)sarcosinate

Guidance literature:

methyl N-(benzyloxycarbonyl)sarcosinate; With potassium hexamethylsilazane; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; With ferrocenium hexafluorophosphate; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/adsc.202100964

upstream raw materials:

diazomethane

N-(Benzyloxycarbonyl)sarcosine

N-methylglycine methyl ester hydrochloride

benzyl chloroformate

Downstream raw materials:

(+/-)-N-benzyloxycarbonyl-N-methyl-glycine-(cis-2-hydroxy-cyclohexylamide)

[(S)-1-{trans-4-[2-(benzyloxycarbonyl-methyl-amino)-acetylamino]-cyclohexyl}-2-(3,3-difluoro-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester