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Technology Process of tert-butyl N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-N6-(tert-butoxycarbonyl)-D-lysinate

tert-butyl N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-N6-(tert-butoxycarbonyl)-D-lysinate

Base Information
  • Chemical Name:tert-butyl N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-N6-(tert-butoxycarbonyl)-D-lysinate
  • CAS No.:917886-89-6
  • Molecular Formula:C43H53FN4O11S
  • Molecular Weight:852.978
  • Hs Code.:
tert-butyl N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-N<sub>6</sub>-(tert-butoxycarbonyl)-D-lysinate

Synonyms:tert-butyl N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-N6-(tert-butoxycarbonyl)-D-lysinate

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Chemical Property of tert-butyl N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-N6-(tert-butoxycarbonyl)-D-lysinate
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Technology Process of tert-butyl N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-N6-(tert-butoxycarbonyl)-D-lysinate

There total 12 articles about tert-butyl N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-N6-(tert-butoxycarbonyl)-D-lysinate 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:

NH<sub>2</sub>-D-Lys(Boc)-Ot-Bu*HCl
201007-86-5

NH2-D-Lys(Boc)-Ot-Bu*HCl

N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycine
917886-84-1

N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycine

tert-butyl N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-N<sub>6</sub>-(tert-butoxycarbonyl)-D-lysinate
917886-89-6

tert-butyl N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-N6-(tert-butoxycarbonyl)-D-lysinate

Guidance literature:
With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In dichloromethane; at 18 - 25 ℃; for 3h;

Reference yield:

1-(benzo[1,3]dioxol-5-yl)-2-bromoethanone
40288-65-1

1-(benzo[1,3]dioxol-5-yl)-2-bromoethanone

tert-butyl N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-N<sub>6</sub>-(tert-butoxycarbonyl)-D-lysinate
917886-89-6

tert-butyl N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-N6-(tert-butoxycarbonyl)-D-lysinate

Guidance literature:
Multi-step reaction with 11 steps
1.1: potassium carbonate / acetone / 7 h / Heating / reflux
2.1: toluene-4-sulfonic acid / benzene / 2 h / Heating / reflux
3.1: lithium hydroxide; water / tetrahydrofuran / 19 h / 0 - 25 °C
3.2: pH 3
4.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 0.33 h / 0 °C
4.2: 16 h / 18 - 25 °C
5.1: titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / 0.83 h / 0 °C
5.2: 0.83 h / -30 °C
5.3: 1.67 h / -30 °C
6.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 1 h / 90 °C
6.2: 1 h / 45 °C
7.1: formic acid / 2 h / 18 - 25 °C
8.1: 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane / 18 - 25 °C
9.1: trifluoroacetic acid / dichloromethane / 1 h
10.1: sodium tetrahydroborate / methanol / 0.67 h
11.1: 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane / 3 h / 18 - 25 °C
With 4-methyl-morpholine; titanium(IV) isopropylate; dmap; lithium hydroxide; sodium tetrahydroborate; formic acid; N,O-bis-(trimethylsilyl)-acetamide; water; titanium tetrachloride; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; dicyclohexyl-carbodiimide; trifluoroacetic acid; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; benzene;

Reference yield:

4-fluoroaniline
371-40-4

4-fluoroaniline

tert-butyl N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-N<sub>6</sub>-(tert-butoxycarbonyl)-D-lysinate
917886-89-6

tert-butyl N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-N6-(tert-butoxycarbonyl)-D-lysinate

Guidance literature:
Multi-step reaction with 11 steps
1.1: toluene-4-sulfonic acid / toluene / 2 h / Heating / reflux
2.1: titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / 0.92 h / 0 °C
2.2: 0.83 h / -40 °C
3.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 1 h / 90 °C
3.2: 24 h / 45 °C
4.1: dichloromethane / 3 h / 0 - 25 °C
5.1: water; triphenylphosphine / acetone / 0.5 h
6.1: triethylamine / dichloromethane / 18 h / 18 - 25 °C
7.1: formic acid / 1.5 h / 18 - 25 °C
8.1: 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane / 18 - 25 °C
9.1: trifluoroacetic acid / dichloromethane / 1 h
10.1: sodium tetrahydroborate / methanol / 0.67 h
11.1: 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane / 3 h / 18 - 25 °C
With 4-methyl-morpholine; titanium(IV) isopropylate; sodium tetrahydroborate; formic acid; N,O-bis-(trimethylsilyl)-acetamide; water; titanium tetrachloride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; triphenylphosphine; trifluoroacetic acid; toluene-4-sulfonic acid; In methanol; dichloromethane; acetone; toluene;
upstream raw materials:

NH2-D-Lys(Boc)-Ot-Bu*HCl

N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycine

(3R,4R)-1-(4-fluorophenyl)-3-[(3-nitropyridin-2-yl)dithio]-4-[4-(t-butoxycarbonylmethoxy)phenyl]azetidin-2-one

tert-butyl (4-{(E)-[(4-fluorophenyl)imino]methyl}phenoxy)acetate

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