N-Acetyl-L-cysteine methyl ester

Base Information

• Chemical Name: N-Acetyl-L-cysteine methyl ester
• CAS No.: 7652-46-2
• Molecular Formula: C6H11NO3S
• Molecular Weight: 177.224
• Hs Code.: 2930909090
• European Community (EC) Number: 819-083-7
• DSSTox Substance ID: DTXSID40227330
• Nikkaji Number: J306.150G
• Wikidata: Q76390961
• Mol file: 7652-46-2.mol

Synonyms:7652-46-2;N-Acetyl-L-cysteine methyl ester;(R)-methyl 2-acetamido-3-mercaptopropanoate;L-Cysteine,N-acetyl-, methyl ester;methyl (2R)-2-acetamido-3-sulfanylpropanoate;Methyl acetyl-L-cysteinate;L-Cysteine, N-acetyl-, methyl ester;n-acetylcysteine methyl ester;MFCD00237476;SCHEMBL112332;DTXSID40227330;QTKAQJWFVXPIFV-YFKPBYRVSA-N;AKOS015906923;AS-10678;HY-23174;5,6-DICHLORONICOTINICACIDETHYLESTER;(R)-methyl2-acetamido-3-mercaptopropanoate;CS-0047728;EN300-197716;methyl (2R)-2-acetamido-3-sulfanyl-propanoate;A838735;N-Acetyl-L-cysteine methyl ester (Ac-L-Cys-OMe);N-Acetyl-L-cysteine methyl ester, >=90% (HPLC);(2R)-2-acetamido-3-mercaptopropanoic acid methyl ester

Chemical Property of N-Acetyl-L-cysteine methyl ester

Chemical Property:

• Vapor Pressure: 0.000216mmHg at 25°C
• Melting Point: 77-81 °C
• Refractive Index: 1.481
• Boiling Point: 326.402 °C at 760 mmHg
• PKA: 9.13±0.10(Predicted)
• Flash Point: 151.203 °C
• PSA: 97.69000
• Density: 1.17 g/cm³
• LogP: 0.43420
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 177.04596439
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

98% ^*data from raw suppliers

N-Acetyl-L-cysteine methyl ester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC(CS)C(=O)OC
• Isomeric SMILES: CC(=O)N[C@@H](CS)C(=O)OC
• Uses: N-Acetyl-L-cysteine Methyl Ester is used in the preparation of benzyl mono-fluorophosphonate and benzyl penta-fluorophosphate anions as physiologically stable phosphotyrosine mimetics and inhibitors of protein tyrosine phosphatases. It can also be used in the preparation of anthracene derivatives.

Technology Process of N-Acetyl-L-cysteine methyl ester

There total 32 articles about N-Acetyl-L-cysteine methyl ester 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%

methanol (67-56-1) + N-acetylcystein (616-91-1,7696-05-1) → Ac-Cys-OMe (7652-46-2)

Guidance literature:

With acetyl chloride; at 20 ℃; for 48h;

Reference yield: 98.0%

(R)-2-Acetylamino-3-tritylsulfanyl-propionic acid methyl ester → Ac-Cys-OMe (7652-46-2)

Guidance literature:

With triethylsilane; In dichloromethane; trifluoroacetic acid; at 0 ℃;

DOI:10.1039/c3cp50743b

Reference yield: 95.0%

C25H25N2O5PS (1071983-22-6) → 2-acetylamino-3-mercapto-propionic acid methyl ester (7652-46-2,118398-49-5) + 2-(diphenylphosphoryl)benzamide (1071983-26-0)

Guidance literature:

With 2-diphenylphosphanyl benzoic acid phenyl ester; In tetrahydrofuran; water; acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1002/anie.200801654

upstream raw materials:

N,N'-diacetyl-L-cystine dimethyl ester

methanol

N-acetylcystein

methyl N,S-diacetylcysteinate

Downstream raw materials:

2-Acetylamino-3-(2-oxo-ethylsulfanyl)-propionic acid methyl ester

2-Acetylamino-3-[2-(2-hydroxy-ethoxycarbonyl)-propylsulfanyl]-propionic acid methyl ester

C₁₉H₂₀N₂O₄SSe

2-<2-S-(N-acetylcysteinyl)ethylthio>ethanol methyl ester

Refernces

• 1、 Suarez-Moreira, Edward,Hannibal, Luciana,Smith, Clyde A.,Chavez, Roberto A.,Jacobsen, Donald W.,Brasch, Nicola E.. "A simple, convenient method to synthesize cobalamins: Synthesis of homocysteinylcobalamin, N-acetylcysteinylcobalamin, 2-N-acetylamino-2- carbomethoxyethanethiolatocobalamin, sulfitocobalamin and nitrocobalamin". . p. 5269 - 5277. Retrieved 2006.
• 2、 Fu, Hua,Li, Hongyun,Li, Youshan,Lou, Zhenbang,Yang, Haijun,Zhao, Yufen. "Bioorthogonal Ligation and Cleavage by Reactions of Chloroquinoxalines with ortho-Dithiophenols". supporting information. p. 3671 - 3677. Retrieved 2020/02/04.