Methyl N-[(benzyloxy)carbonyl]glycyl-N-methylglycinate

Base Information

• Chemical Name: Methyl N-[(benzyloxy)carbonyl]glycyl-N-methylglycinate
• CAS No.: 62246-18-8
• Molecular Formula: C14H18N2O5
• Molecular Weight: 294.3031
• NSC Number: 169142
• DSSTox Substance ID: DTXSID40305107
• Nikkaji Number: J2.505.884D
• Wikidata: Q82051569
• Mol file: 62246-18-8.mol

Synonyms:62246-18-8;NSC169142;DTXSID40305107;NSC-169142;Methyl N-[(benzyloxy)carbonyl]glycyl-N-methylglycinate

Chemical Property of Methyl N-[(benzyloxy)carbonyl]glycyl-N-methylglycinate

Chemical Property:

• Vapor Pressure: 5.04E-09mmHg at 25°C
• Boiling Point: 470.5°Cat760mmHg
• Flash Point: 238.3°C
• Density: 1.218g/cm³
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 294.12157168
• Heavy Atom Count: 21
• Complexity: 366

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl N-[(benzyloxy)carbonyl]glycyl-N-methylglycinate

There total 1 articles about Methyl N-[(benzyloxy)carbonyl]glycyl-N-methylglycinate 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: 80.0%

benzyl [2?(1H?benzo[d][1,2,3]triazol?1?yl)?2?oxoethyl]carbamate (173459-80-8) + N-methylglycine methylester (5473-12-1) → methyl 2-[(2-[[(benzyloxy)carbonyl]amino]acetyl)(methyl)amino]acetate (62246-18-8)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 55 - 60 ℃; for 1h; microwave irradiation;

DOI:10.1021/jo0704255

Reference yield:

methyl 2-[(2-[[(benzyloxy)carbonyl]amino]acetyl)(methyl)amino]acetate (62246-18-8) → {[2-((R)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-acetyl]-methyl-amino}-acetic acid (175444-30-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1 N aq. HCl, H₂ / Pd/C / methanol / 0.5 h / 760 Torr

2: 1.) 1-hydroxybenzotriazole, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 2.) N,N-diisopropylethylamine / 1.) DMF, 0 deg C, 15 min, 2.) DMF, RT, 15 h

3: 100 percent / LiOH / methanol; tetrahydrofuran; H₂O / 1 h / Ambient temperature

With hydrogenchloride; lithium hydroxide; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; water;

DOI:10.1016/S0040-4020(96)00068-3

Reference yield:

methyl 2-[(2-[[(benzyloxy)carbonyl]amino]acetyl)(methyl)amino]acetate (62246-18-8) → {[2-((R)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-acetyl]-methyl-amino}-acetic acid methyl ester (175444-32-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1 N aq. HCl, H₂ / Pd/C / methanol / 0.5 h / 760 Torr

2: 1.) 1-hydroxybenzotriazole, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 2.) N,N-diisopropylethylamine / 1.) DMF, 0 deg C, 15 min, 2.) DMF, RT, 15 h

With hydrogenchloride; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol;

DOI:10.1016/S0040-4020(96)00068-3

upstream raw materials:

benzyl [2?(1H?benzo[d][1,2,3]triazol?1?yl)?2?oxoethyl]carbamate

N-methylglycine methylester

Downstream raw materials:

{[2-((R)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-acetyl]-methyl-amino}-acetic acid

{[2-((R)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-acetyl]-methyl-amino}-acetic acid methyl ester