Deacetyl Racecadotril Disulfide

Base Information

• Chemical Name: Deacetyl Racecadotril Disulfide
• CAS No.: 141437-88-9
• Molecular Formula: C₃₈H₄₀N₂O₆S₂
• Molecular Weight: 684.877
• UNII: XFE6MG8RXU
• Mol file: 141437-88-9.mol

Synonyms:141437-88-9;Deacetyl Racecadotril Disulfide;UNII-XFE6MG8RXU;dibenzyl 2,2'-((3,3'-disulfanediylbis(2-benzylpropanoyl))bis(azanediyl))diacetate;XFE6MG8RXU;Deacetyl racecadotril dimer;benzyl 2-[[2-benzyl-3-[[2-benzyl-3-oxo-3-[(2-oxo-2-phenylmethoxyethyl)amino]propyl]disulfanyl]propanoyl]amino]acetate;Dibenzyl 5,10-dibenzyl-4,11-dioxo-7,8-dithia-3,12-diazatetradecanedioate;benzyl 2-(2-{[(2-benzyl-2-{[2-(benzyloxy)-2-oxoethyl]carbamoyl}ethyl)disulfanyl]methyl}-3-phenylpropanamido)acetate;Glycine, N,N'-(dithiobis(1-oxo-2-(phenylmethyl)-3,1-propanediyl))bis-, bis(phenylmethyl) ester;Racecadotril impurity H [EP];RACECADOTRIL IMPURITY H [EP IMPURITY];G71699

Chemical Property of Deacetyl Racecadotril Disulfide

Chemical Property:

• Melting Point: 92-94°C
• Boiling Point: 866.2±65.0 °C(Predicted)
• PKA: 13.43±0.46(Predicted)
• Density: 1.245±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 21
• Exact Mass: 684.23277935
• Heavy Atom Count: 48
• Complexity: 883

Purity/Quality:

> 95% ^*data from raw suppliers

DeacetylRacecadotrilDisulfide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(CSSCC(CC2=CC=CC=C2)C(=O)NCC(=O)OCC3=CC=CC=C3)C(=O)NCC(=O)OCC4=CC=CC=C4
• Uses: Deacetyl Racecadotril Disulfide is an impurity of Racecadotril (R070600); an antidiarrheal and enkephalinase inhibitor that reduces the amount of water and electrolytes into the intestine.

Technology Process of Deacetyl Racecadotril Disulfide

There total 3 articles about Deacetyl Racecadotril Disulfide 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: 87.0%

Gly-OBz (1738-68-7) + 2-(2-Carboxy-3-phenyl-propyldisulfanylmethyl)-3-phenyl-propionic acid (141437-87-8) → {2-[2-(Benzyloxycarbonylmethyl-carbamoyl)-3-phenyl-propyldisulfanylmethyl]-3-phenyl-propionylamino}-acetic acid benzyl ester (141437-88-9)

Guidance literature:

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; chloroform; Ambient temperature;

DOI:10.1021/jm00091a016

Reference yield:

2-mercaptomethyl-3-phenylpropanoic acid (81110-55-6,69734-01-6) → {2-[2-(Benzyloxycarbonylmethyl-carbamoyl)-3-phenyl-propyldisulfanylmethyl]-3-phenyl-propionylamino}-acetic acid benzyl ester (141437-88-9)

Guidance literature:

Multi-step reaction with 2 steps

1: I₂ / ethanol; H₂O

2: 87 percent / Et₃N, 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / tetrahydrofuran; CHCl₃ / Ambient temperature

With iodine; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethanol; chloroform; water;

DOI:10.1021/jm00091a016

Reference yield:

3-acetylthio-2-benzylpropanoic acid (91702-98-6,80969-99-9) → {2-[2-(Benzyloxycarbonylmethyl-carbamoyl)-3-phenyl-propyldisulfanylmethyl]-3-phenyl-propionylamino}-acetic acid benzyl ester (141437-88-9)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. NaOH / ethanol / 1.5 h / 0 - 20 °C

2: I₂ / ethanol; H₂O

3: 87 percent / Et₃N, 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / tetrahydrofuran; CHCl₃ / Ambient temperature

With sodium hydroxide; iodine; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethanol; chloroform; water;

DOI:10.1021/jm00091a016

upstream raw materials:

Gly-OBz

2-(2-Carboxy-3-phenyl-propyldisulfanylmethyl)-3-phenyl-propionic acid

2-mercaptomethyl-3-phenylpropanoic acid

3-acetylthio-2-benzylpropanoic acid

Downstream raw materials:

N-(2-mercaptomethyl-3-phenyl-1-oxopropyl)-glycine benzyl ester

[2-((S)-2-Amino-4-methyl-pentyldisulfanylmethyl)-3-phenyl-propionylamino]-acetic acid benzyl ester

[2-((S)-2-Amino-3-phenyl-propyldisulfanylmethyl)-3-phenyl-propionylamino]-acetic acid benzyl ester

[2-((S)-2-Amino-4-methylsulfanyl-butyldisulfanylmethyl)-3-phenyl-propionylamino]-acetic acid benzyl ester