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

Base Information

Chemical Name:N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-L-tryptophan
CAS No.:858104-63-9
Molecular Formula:C₃₆H₃₁F₂N₃O₆S
Molecular Weight:671.721
Hs Code.:

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

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

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

There total 9 articles about N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-L-tryptophan 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: 58.0%

: 858104-50-4
(4-{(2R,3R)-1-(4-fluoro-phenyl)-3-[(RS)-2-(4-fluoro-phenyl)-2-oxoethylsulfanyl]-4-oxo-azetidin-2-yl}-phenoxy)-acetic acid

: (+/-)-Tryptophan tert-butyl ester hydrochloride

: 858104-63-9
N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-L-tryptophan

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; (+/-)-Tryptophan tert-butyl ester hydrochloride; With 4-methyl-morpholine; In dichloromethane; at 18 - 25 ℃; for 0.166667h;

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In dichloromethane; at 18 - 25 ℃; for 6h;

With sodium tetrahydroborate; ammonium acetate; water; trifluoroacetic acid; more than 3 stages;

Reference yield:

: C₃₆H₂₉F₂N₃O₆S

: 858104-63-9
N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-L-tryptophan

Guidance literature:: C₃₆H₂₉F₂N₃O₆S; With sodium tetrahydroborate; In methanol; for 0.0833333h;

With ammonium acetate; water; In methanol;

Reference yield:

: 66560-19-8
ethyl 2-((2-oxo-2-phenylethyl)thio)acetate

: 858104-63-9
N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-L-tryptophan

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 / dichloromethane / 0.17 h

7.2: 4 h

8.1: trifluoroacetic acid / dichloromethane / 4 h

9.1: sodium tetrahydroborate / methanol / 0.08 h

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