(R)-2-amino-N-(4-(((2S,5R)-5-((R)-(3-chlorophenyl)(hydroxy)methyl)pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-cyclopenta[d]thiazole-4-carboxamide

Base Information

Chemical Name:(R)-2-amino-N-(4-(((2S,5R)-5-((R)-(3-chlorophenyl)(hydroxy)methyl)pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-cyclopenta[d]thiazole-4-carboxamide
CAS No.:1190391-17-3
Molecular Formula:C₂₅H₂₇ClN₄O₂S
Molecular Weight:483.034
Hs Code.:

(R)-2-amino-N-(4-(((2S,5R)-5-((R)-(3-chlorophenyl)(hydroxy)methyl)pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-cyclopenta[d]thiazole-4-carboxamide

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Chemical Property of (R)-2-amino-N-(4-(((2S,5R)-5-((R)-(3-chlorophenyl)(hydroxy)methyl)pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-cyclopenta[d]thiazole-4-carboxamide

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Technology Process of (R)-2-amino-N-(4-(((2S,5R)-5-((R)-(3-chlorophenyl)(hydroxy)methyl)pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-cyclopenta[d]thiazole-4-carboxamide

There total 18 articles about (R)-2-amino-N-(4-(((2S,5R)-5-((R)-(3-chlorophenyl)(hydroxy)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:

: 1558057-87-6
C₃₅H₄₃ClN₄O₆S

: 1190391-17-3
(R)-2-amino-N-(4-(((2S,5R)-5-((R)-(3-chlorophenyl)(hydroxy)methyl)pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-cyclopenta[d]thiazole-4-carboxamide

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 25 ℃; for 2h; Inert atmosphere;
DOI:10.1021/jm4017224

Reference yield:

: 1558057-55-8
4-methoxybenzyl ((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(3-chlorophenyl)-6-(4-nitrophenyl)-5-oxohexan-2-yl)carbamate

: 1190391-17-3
(R)-2-amino-N-(4-(((2S,5R)-5-((R)-(3-chlorophenyl)(hydroxy)methyl)pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-cyclopenta[d]thiazole-4-carboxamide

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:

: 1558057-62-7
(2R,5S)-2-((R)-((tert-butyldimethylsilyl)oxy)(3-chlorophenyl)methyl)-5-(4-nitrobenzyl)pyrrolidine

: 1190391-17-3
(R)-2-amino-N-(4-(((2S,5R)-5-((R)-(3-chlorophenyl)(hydroxy)methyl)pyrrolidin-2-yl)methyl)phenyl)-5,6-dihydro-4H-cyclopenta[d]thiazole-4-carboxamide

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