(1S,4R,5S)-4-(2-Hydroxy-ethyl)-1-((S)-1-hydroxy-2-methyl-propyl)-6-[(S)-1-(4-methoxy-phenyl)-ethyl]-2,6-diaza-bicyclo[3.2.0]heptane-3,7-dione

Base Information

Chemical Name:(1S,4R,5S)-4-(2-Hydroxy-ethyl)-1-((S)-1-hydroxy-2-methyl-propyl)-6-[(S)-1-(4-methoxy-phenyl)-ethyl]-2,6-diaza-bicyclo[3.2.0]heptane-3,7-dione
CAS No.:870528-61-3
Molecular Formula:C₂₀H₂₈N₂O₅
Molecular Weight:376.453
Hs Code.:

Synonyms:(1S,4R,5S)-4-(2-Hydroxy-ethyl)-1-((S)-1-hydroxy-2-methyl-propyl)-6-[(S)-1-(4-methoxy-phenyl)-ethyl]-2,6-diaza-bicyclo[3.2.0]heptane-3,7-dione

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Chemical Property of (1S,4R,5S)-4-(2-Hydroxy-ethyl)-1-((S)-1-hydroxy-2-methyl-propyl)-6-[(S)-1-(4-methoxy-phenyl)-ethyl]-2,6-diaza-bicyclo[3.2.0]heptane-3,7-dione

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Technology Process of (1S,4R,5S)-4-(2-Hydroxy-ethyl)-1-((S)-1-hydroxy-2-methyl-propyl)-6-[(S)-1-(4-methoxy-phenyl)-ethyl]-2,6-diaza-bicyclo[3.2.0]heptane-3,7-dione

There total 13 articles about (1S,4R,5S)-4-(2-Hydroxy-ethyl)-1-((S)-1-hydroxy-2-methyl-propyl)-6-[(S)-1-(4-methoxy-phenyl)-ethyl]-2,6-diaza-bicyclo[3.2.0]heptane-3,7-dione 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%

: 870528-60-2
[(3S,4S)-3-((S)-1-Hydroxy-2-methyl-propyl)-1-[(S)-1-(4-methoxy-phenyl)-ethyl]-2-oxo-4-((R)-2-oxo-tetrahydro-furan-3-yl)-azetidin-3-yl]-carbamic acid tert-butyl ester

: 870528-61-3
(1S,4R,5S)-4-(2-Hydroxy-ethyl)-1-((S)-1-hydroxy-2-methyl-propyl)-6-[(S)-1-(4-methoxy-phenyl)-ethyl]-2,6-diaza-bicyclo[3.2.0]heptane-3,7-dione

Guidance literature:: [(3S,4S)-3-((S)-1-Hydroxy-2-methyl-propyl)-1-[(S)-1-(4-methoxy-phenyl)-ethyl]-2-oxo-4-((R)-2-oxo-tetrahydro-furan-3-yl)-azetidin-3-yl]-carbamic acid tert-butyl ester; With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 23 ℃; for 2h;

With triethylamine trihydrofluoride; In tetrahydrofuran; at 23 ℃; for 1h;
DOI:10.1021/ja056284a

Reference yield:

: 870528-54-4
(4S,5S) 5-isopropyl-2-oxo-oxazolidine-4-carboxylic acid benzyl ester

: 870528-61-3
(1S,4R,5S)-4-(2-Hydroxy-ethyl)-1-((S)-1-hydroxy-2-methyl-propyl)-6-[(S)-1-(4-methoxy-phenyl)-ethyl]-2,6-diaza-bicyclo[3.2.0]heptane-3,7-dione

Guidance literature:: Multi-step reaction with 8 steps

1.1: 99 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 23 °C

2.1: 98 percent / H₂ / Pd/C / ethyl acetate / 6 h / 23 °C

3.1: 1-chloro-N,N,2-trimethyl-1-propenylamine / CH₂Cl₂ / -78 - 23 °C

4.1: 240 mg / triethylamine / CH₂Cl₂ / 0.5 h / 23 °C

5.1: 94 percent / Cs₂CO₃ / methanol / 2 h / 23 °C

6.1: 70 percent / peroxyacetic acid; acetic acid; sodium acetate / CH₂Cl₂ / 18 h / 23 °C

7.1: 91 percent / H₂ / Pd/C / tetrahydrofuran / 24 h / -20 °C

8.1: trimethylsilyl trifluoromethanesulfonate; 2,6-lutidine / CH₂Cl₂ / 2 h / 23 °C

8.2: 85 percent / triethylamine trihydrofluoride / tetrahydrofuran / 1 h / 23 °C

With 2,6-dimethylpyridine; peracetic acid; dmap; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium acetate; caesium carbonate; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1021/ja056284a

Reference yield:

: 125414-69-9
(4S,5S) 5-isopropyl-2-oxo-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester

: 870528-61-3
(1S,4R,5S)-4-(2-Hydroxy-ethyl)-1-((S)-1-hydroxy-2-methyl-propyl)-6-[(S)-1-(4-methoxy-phenyl)-ethyl]-2,6-diaza-bicyclo[3.2.0]heptane-3,7-dione

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1-chloro-N,N,2-trimethyl-1-propenylamine / CH₂Cl₂ / -78 - 23 °C

2.1: 240 mg / triethylamine / CH₂Cl₂ / 0.5 h / 23 °C

3.1: 94 percent / Cs₂CO₃ / methanol / 2 h / 23 °C

4.1: 70 percent / peroxyacetic acid; acetic acid; sodium acetate / CH₂Cl₂ / 18 h / 23 °C

5.1: 91 percent / H₂ / Pd/C / tetrahydrofuran / 24 h / -20 °C

6.1: trimethylsilyl trifluoromethanesulfonate; 2,6-lutidine / CH₂Cl₂ / 2 h / 23 °C

6.2: 85 percent / triethylamine trihydrofluoride / tetrahydrofuran / 1 h / 23 °C

With 2,6-dimethylpyridine; peracetic acid; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium acetate; caesium carbonate; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja056284a