(S)-4-Acetamido-5-methoxy-5-oxopentanoic acid

Base Information

• Chemical Name: (S)-4-Acetamido-5-methoxy-5-oxopentanoic acid
• CAS No.: 17015-15-5
• Molecular Formula: C₈H₁₃NO₅
• Molecular Weight: 203.195
• DSSTox Substance ID: DTXSID00427359
• Wikidata: Q72435229
• Mol file: 17015-15-5.mol

Synonyms:Ac-glu-ome;17015-15-5;(S)-4-Acetamido-5-methoxy-5-oxopentanoic acid;(4S)-4-acetamido-5-methoxy-5-oxopentanoic acid;Acetyl-L-glutamic acid alpha-methyl ester;SCHEMBL4577282;DTXSID00427359;AMY22573;MFCD00080830;FD21497;AS-49094;L-Glutamic acid,N-acetyl-,1-methyl ester;CS-0208592;N-alpha-Acetyl-L-glutamic acid alpha-methyl ester;J-010602

Chemical Property of (S)-4-Acetamido-5-methoxy-5-oxopentanoic acid

Chemical Property:

• Boiling Point: 443.513 °C at 760 mmHg
• PKA: 4.42±0.10(Predicted)
• Flash Point: 222.029 °C
• PSA: 92.70000
• Density: 1.231 g/cm³
• LogP: -0.08020
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 203.07937252
• Heavy Atom Count: 14
• Complexity: 238

Purity/Quality:

99.3% ^*data from raw suppliers

Acetyl-L-glutamic acid alpha-methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CCC(=O)O)C(=O)OC
• Isomeric SMILES: CC(=O)N[C@@H](CCC(=O)O)C(=O)OC

Technology Process of (S)-4-Acetamido-5-methoxy-5-oxopentanoic acid

There total 1 articles about (S)-4-Acetamido-5-methoxy-5-oxopentanoic 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%

L-glutamic acid 5-tert-butyl 1-methyl ester hydrochloride (6234-01-1,16948-36-0) + acetic anhydride (108-24-7) → 1-methyl N-acetyl-L-glutamic acid (150857-81-1,17015-15-5)

Guidance literature:

L-glutamic acid 5-tert-butyl 1-methyl ester hydrochloride; With triethylamine; In dichloromethane; at 0 ℃; for 0.0833333h; Inert atmosphere;

acetic anhydride; In dichloromethane; at 20 ℃; for 17h; Inert atmosphere;

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.1c03344

Reference yield:

C11H10F3N3O2 + 1-methyl N-acetyl-L-glutamic acid (150857-81-1,17015-15-5) → C19H23F3N2O7

Guidance literature:

In neat (no solvent); at 4 ℃; for 0.1h; Photolysis; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.1c02509

Reference yield:

1-methyl N-acetyl-L-glutamic acid (150857-81-1,17015-15-5) → C31H44N4O12S2 (936952-13-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 92 percent / DCC / tetrahydrofuran / 19 h / 0 - 5 °C

2.1: TFA / 2 h / 20 °C

3.1: TEA; isobutyl chloroformate / dimethylformamide / 0.25 h / -15 °C

3.2: dimethylformamide / 19 h / 0 - 5 °C

With TEA; dicyclohexyl-carbodiimide; trifluoroacetic acid; isobutyl chloroformate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm070037v

upstream raw materials:

L-glutamic acid 5-tert-butyl 1-methyl ester hydrochloride

acetic anhydride

Downstream raw materials:

C₃₁H₄₄N₄O₁₂S₂

C₂₃H₃₂N₄O₁₀S

C₂₉H₄₀N₄O₁₂S

Refernces