(R)-2-(4-fluorophenyl)-N-(4-(((2S,5R)-5-((R)-hydroxy(phenyl)-methyl)pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-cyclopenta[d]thiazole-4-carboxamide

Base Information

• Chemical Name: (R)-2-(4-fluorophenyl)-N-(4-(((2S,5R)-5-((R)-hydroxy(phenyl)-methyl)pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-cyclopenta[d]thiazole-4-carboxamide
• CAS No.: 1190389-31-1
• Molecular Formula: C₃₁H₃₀FN₃O₂S
• Molecular Weight: 527.663
• Mol file: 1190389-31-1.mol

Synonyms:

Chemical Property of (R)-2-(4-fluorophenyl)-N-(4-(((2S,5R)-5-((R)-hydroxy(phenyl)-methyl)pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-cyclopenta[d]thiazole-4-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-(4-fluorophenyl)-N-(4-(((2S,5R)-5-((R)-hydroxy(phenyl)-methyl)pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-cyclopenta[d]thiazole-4-carboxamide

There total 17 articles about (R)-2-(4-fluorophenyl)-N-(4-(((2S,5R)-5-((R)-hydroxy(phenyl)-methyl)pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-cyclopenta[d]thiazole-4-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:

C36H38FN3O4S (1558058-09-5) → (R)-2-(4-fluorophenyl)-N-(4-(((2S,5R)-5-((R)-hydroxy(phenyl)-methyl)pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-cyclopenta[d]thiazole-4-carboxamide (1190389-31-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 25 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm4017224

Reference yield:

4-methoxybenzyl ((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-6-(4-nitrophenyl)-5-oxo-1-phenylhexan-2-yl)carbamate (1190391-66-2) → (R)-2-(4-fluorophenyl)-N-(4-(((2S,5R)-5-((R)-hydroxy(phenyl)-methyl)pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-cyclopenta[d]thiazole-4-carboxamide (1190389-31-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: trifluoroacetic acid / dichloromethane / 1.5 h / Inert atmosphere

2.1: sodium tris(acetoxy)borohydride / dichloromethane / 12 h / 0 - 25 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 °C / Inert atmosphere

4.1: hydrogen; palladium 10% on activated carbon / methanol / 12 h

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere; Heating

6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 4 h / 25 °C / Inert atmosphere

6.2: chiral HPLC(Pirkle (R,R)-Whelk-O column / Inert atmosphere

7.1: trifluoroacetic acid / dichloromethane / 2 h / 25 °C / Inert atmosphere

With palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm4017224

Reference yield:

(2R,5S)-2-((R)-((tert-butyldimethylsilyl)oxy)(phenyl)methyl)-5-(4-nitrobenzyl)pyrrolidine (1190391-67-3) → (R)-2-(4-fluorophenyl)-N-(4-(((2S,5R)-5-((R)-hydroxy(phenyl)-methyl)pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-cyclopenta[d]thiazole-4-carboxamide (1190389-31-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 °C / Inert atmosphere

2.1: hydrogen; palladium 10% on activated carbon / methanol / 12 h

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere; Heating

4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 4 h / 25 °C / Inert atmosphere

4.2: chiral HPLC(Pirkle (R,R)-Whelk-O column / Inert atmosphere

5.1: trifluoroacetic acid / dichloromethane / 2 h / 25 °C / Inert atmosphere

With palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm4017224

upstream raw materials:

4-methoxybenzyl ((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-6-(4-nitrophenyl)-5-oxo-1-phenylhexan-2-yl)carbamate

(2R,5S)-2-((R)-((tert-butyldimethylsilyl)oxy)(phenyl)methyl)-5-(4-nitrobenzyl)pyrrolidine

tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-5-(4-nitrobenzyl)pyrrolidine-1-carboxylate

tert-butyl (2S,5R)-2-(4-aminobenzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidine-1-carboxylate

Refernces