N(Im)-Ethoxycarbonyl-S-ethoxycarbonyl L-Ergothioneine Methyl Ester Iodide

Base Information

• Chemical Name: N(Im)-Ethoxycarbonyl-S-ethoxycarbonyl L-Ergothioneine Methyl Ester Iodide
• CAS No.: 162240-57-5
• Molecular Formula: C₁₆H₂₆N₃O₆S*I
• Molecular Weight: 515.369
• DSSTox Substance ID: DTXSID40434406
• Mol file: 162240-57-5.mol

Synonyms:162240-57-5;N(Im)-Ethoxycarbonyl-S-ethoxycarbonyl L-Ergothioneine Methyl Ester Iodide;[(2S)-3-(1-ethoxycarbonyl-2-ethoxycarbonylsulfanylimidazol-4-yl)-1-methoxy-1-oxopropan-2-yl]-trimethylazanium;iodide;1H-Imidazole-4-ethanaminium, 1-(ethoxycarbonyl)-2-[(ethoxycarbonyl)thio]-alpha-(methoxycarbonyl)-N,N,N-trimethyl-, iodide, (S)- (9CI);DTXSID40434406;CQVZBTBSURUDKC-YDALLXLXSA-M;AKOS030243360;J-009908

Chemical Property of N(Im)-Ethoxycarbonyl-S-ethoxycarbonyl L-Ergothioneine Methyl Ester Iodide

Chemical Property:

• PSA: 122.02000
• LogP: -1.06940
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 515.05870
• Heavy Atom Count: 27
• Complexity: 511

Purity/Quality:

95% ^*data from raw suppliers

N(Im)-Ethoxycarbonyl-S-ethoxycarbonylL-ErgothioneineMethylEsterIodide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)N1C=C(N=C1SC(=O)OCC)CC(C(=O)OC)[N+](C)(C)C.[I-]
• Isomeric SMILES: CCOC(=O)N1C=C(N=C1SC(=O)OCC)C[C@@H](C(=O)OC)[N+](C)(C)C.[I-]

Technology Process of N(Im)-Ethoxycarbonyl-S-ethoxycarbonyl L-Ergothioneine Methyl Ester Iodide

There total 5 articles about N(Im)-Ethoxycarbonyl-S-ethoxycarbonyl L-Ergothioneine Methyl Ester Iodide 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: 85.0%

methyl (S)-3-<1-(ethoxycarbonyl)-2-<(ethoxycarbonyl)thio>-1H-imidazol-4-yl>-2-(dimethylamino)propionate (162138-72-9) + methyl iodide (74-88-4) → methyl (S)-3-<1-(ethoxycarbonyl)-2-<(ethoxycarbonyl)thio>-1H-imidazol-4-yl>-2-(trimethylammonio)propionate iodide (162240-57-5)

Guidance literature:

In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1021/jo00125a014

Reference yield:

l-histidine methyl ester dihydrochloride (4467-54-3,5619-10-3,7389-87-9,18684-16-7,22888-60-4,32381-17-2,92742-29-5,100009-20-9) → methyl (S)-3-<1-(ethoxycarbonyl)-2-<(ethoxycarbonyl)thio>-1H-imidazol-4-yl>-2-(trimethylammonio)propionate iodide (162240-57-5)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Pd/C / H₂O / 5 h / 3800 Torr / Ambient temperature

2: 1.) NaHCO₃, ClC(S)OPh, 2.) TEA / 1.) H₂O, THF, room temperature, 5 h, 2.) MeOH, room temperature, 18 h

3: 99 percent / Et₃N / CH₂Cl₂ / 0.5 h / 10 °C

4: 85 percent / tetrahydrofuran / 24 h / Ambient temperature

With TEA; hydrogen; sodium hydrogencarbonate; triethylamine; phenylcarbonochloridothioate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo00125a014

Reference yield:

methyl (S)-3-(2-mercapto-1H-imidazol-4-yl)-2-(dimethylamino)propionate (162138-71-8) → methyl (S)-3-<1-(ethoxycarbonyl)-2-<(ethoxycarbonyl)thio>-1H-imidazol-4-yl>-2-(trimethylammonio)propionate iodide (162240-57-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / Et₃N / CH₂Cl₂ / 0.5 h / 10 °C

2: 85 percent / tetrahydrofuran / 24 h / Ambient temperature

With triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00125a014

upstream raw materials:

methyl (S)-3-<1-(ethoxycarbonyl)-2-<(ethoxycarbonyl)thio>-1H-imidazol-4-yl>-2-(dimethylamino)propionate

methyl iodide

l-histidine methyl ester dihydrochloride

methyl (S)-3-(2-mercapto-1H-imidazol-4-yl)-2-(dimethylamino)propionate