(2S,4R)-N-[(1S,2R)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide

Base Information

• Chemical Name: (2S,4R)-N-[(1S,2R)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
• CAS No.: 16684-06-3
• Molecular Formula: C₁₈H₃₃ClN₂O₅S
• Molecular Weight: 424.989
• UNII: ST54QM406G
• Nikkaji Number: J360.173K
• Mol file: 16684-06-3.mol

Synonyms:16684-06-3;Epiclindamycin;7-Epiclindamycin;Antibiotic U 21251F;ST54QM406G;(2S,4R)-N-((1S,2R)-2-Chloro-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)propyl)-1-methyl-4-propylpyrrolidine-2-carboxamide;(2S,4R)-N-[(1S,2R)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide;7-Epi Clindamycin Hydrochloride;7-Epiclindamycin [USP];UNII-ST54QM406G;7-EPICLINDAMYCIN [USP IMPURITY];Clindamycin hydrochloride impurity C [EP];A899388;CLINDAMYCIN HYDROCHLORIDE IMPURITY C [EP IMPURITY];D-ERYTHRO-.ALPHA.-D-GALACTO-OCTOPYRANOSIDE, METHYL 7-CHLORO-6,7,8-TRIDEOXY-6-((((2S,4R)-1-METHYL-4-PROPYL-2-PYRROLIDINYL)CARBONYL)AMINO)-1-THIO-;D-Erythro-alpha-D-galacto-octopyranoside, methyl 7-chloro-6,7,8-trideoxy-6-((((2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl)carbonyl)amino)-1-thio-;METHYL 7-CHLORO-6,7,8-TRIDEOXY-6-((((2S,4R)-1-METHYL-4-PROPYLPYRROLIDIN-2-YL)CARBONYL)AMINO)-1-THIO-D-ERYTHRO-.ALPHA.-D-GALACTO-OCTOPYRANOSIDE;Methyl 7-chloro-6,7,8-trideoxy-6-((((2S,4R)-1-methyl-4-propylpyrrolidin-2-yl)carbonyl)amino)-1-thio-D-erythro-alpha-D-galacto-octopyranoside

Chemical Property of (2S,4R)-N-[(1S,2R)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide

Chemical Property:

• Melting Point: >55°C
• Boiling Point: 628.1±55.0 °C(Predicted)
• PKA: 12.87±0.70(Predicted)
• PSA: 127.56000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 0.71830
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly), Water (Slightly, Heated)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 424.1798710
• Heavy Atom Count: 27
• Complexity: 502

Purity/Quality:

97% ^*data from raw suppliers

7-Epi-Clindamycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC1CC(N(C1)C)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)Cl
• Isomeric SMILES: CCC[C@@H]1C[C@H](N(C1)C)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@@H](C)Cl
• Uses: Clindamycin (C580000) impurity in bulk drug. 7-Epiclindamycin (Clindamycin EP Impurity C) is an epimer of Clindamycin (C580000), which is a semi-synthetic antibiotic prepared from Lincomycin, an antibacterial. In addition, 7-Epiclindamycin is an intermediate in synthesizing 7-Epiclindamycin 2-Phosphate (>90%) (E582505), which is an another impurity of Clindamycin.

Technology Process of (2S,4R)-N-[(1S,2R)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide

There total 3 articles about (2S,4R)-N-[(1S,2R)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide 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:

lincomycin hydrochloride (859-18-7) → clindamycin (16684-06-3,18323-44-9,51064-35-8)

Guidance literature:

lincomycin hydrochloride; With phosgene; In chloroform; N,N-dimethyl-formamide; at 5 - 71 ℃; for 2h; Large scale;

at 10 ℃; Temperature; Reagent/catalyst; Alkaline conditions; Large scale;

Reference yield:

→ clindamycin (16684-06-3,18323-44-9,51064-35-8)

Guidance literature:

Reference yield:

→ 7-Chlor-7-deoxylincomycin (16684-06-3,18323-44-9,51064-35-8)

Guidance literature:

Lincomycin*HCl, SOCl2;

upstream raw materials:

lincomycin hydrochloride

Downstream raw materials:

C₂₁H₃₇ClN₂O₅S

clindamycin hydrochloride