N₂-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-L-glutamine

Base Information

• Chemical Name: N₂-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-L-glutamine
• CAS No.: 858104-64-0
• Molecular Formula: C₃₀H₂₉F₂N₃O₇S
• Molecular Weight: 613.639

Synonyms:N₂-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-L-glutamine

Chemical Property of N₂-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-L-glutamine

Chemical Property:

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Technology Process of N₂-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-L-glutamine

There total 9 articles about N₂-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-L-glutamine 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: 74.0%

(4-{(2R,3R)-1-(4-fluoro-phenyl)-3-[(RS)-2-(4-fluoro-phenyl)-2-oxoethylsulfanyl]-4-oxo-azetidin-2-yl}-phenoxy)-acetic acid (858104-50-4) + L-glutamine t-butyl ester hydrochloride → N2-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-L-glutamine (858104-64-0)

Guidance literature:

(4-{(2R,3R)-1-(4-fluoro-phenyl)-3-[(RS)-2-(4-fluoro-phenyl)-2-oxoethylsulfanyl]-4-oxo-azetidin-2-yl}-phenoxy)-acetic acid; L-glutamine t-butyl ester hydrochloride; With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In dichloromethane; at 18 - 25 ℃; for 1.5h;

With formic acid; at 45 - 50 ℃; for 4h;

With sodium tetrahydroborate; acetic acid; more than 3 stages;

Reference yield:

C30H27F2N3O7S → N2-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-L-glutamine (858104-64-0)

Guidance literature:

C₃₀H₂₇F₂N₃O₇S; With sodium tetrahydroborate; In methanol; for 0.25h;

With acetic acid; In methanol;

Reference yield:

ethyl 2-((2-oxo-2-phenylethyl)thio)acetate (66560-19-8) → N2-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-L-glutamine (858104-64-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: toluene-4-sulfonic acid / toluene / 20 °C / Heating / reflux

2.1: lithium hydroxide; water / tetrahydrofuran / 19 h / 0 °C

2.2: pH 6

3.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 0.33 h / 0 °C

3.2: 70 h / 20 °C

4.1: titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / 0.5 h / 0 °C

4.2: 0.83 h / -40 - 0 °C

5.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 1 h / 90 °C

5.2: 18 h / 45 °C

6.1: methanol; water; triethylamine / 48 h / 50 °C

7.1: 4-methyl-morpholine; (1,1,1-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate / dichloromethane / 1.5 h

8.1: formic acid / 4 h / 45 - 50 °C

9.1: sodium tetrahydroborate / methanol / 0.25 h

With 4-methyl-morpholine; titanium(IV) isopropylate; methanol; dmap; lithium hydroxide; sodium tetrahydroborate; formic acid; (1,1,1-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate; water; titanium tetrachloride; N,O-bis-(trimethylsilyl)-acetamide; triethylamine; dicyclohexyl-carbodiimide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; toluene;

upstream raw materials:

(4-{(2R,3R)-1-(4-fluoro-phenyl)-3-[(RS)-2-(4-fluoro-phenyl)-2-oxoethylsulfanyl]-4-oxo-azetidin-2-yl}-phenoxy)-acetic acid

{[(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}acetic acid

ethyl {[(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}acetate

(4S)-3-({[(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}acetyl)-4-phenyl-1,3-oxazolidin-2-one

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