3-{(2R,3S)-1-(4-Nitro-benzyloxycarbonylmethyl)-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid phenyl ester

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Chemical Name:3-{(2R,3S)-1-(4-Nitro-benzyloxycarbonylmethyl)-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid phenyl ester
CAS No.:140866-88-2
Molecular Formula:C₃₃H₃₂N₄O₉
Molecular Weight:628.638
Hs Code.:

Synonyms:3-{(2R,3S)-1-(4-Nitro-benzyloxycarbonylmethyl)-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid phenyl ester

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Chemical Property of 3-{(2R,3S)-1-(4-Nitro-benzyloxycarbonylmethyl)-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid phenyl ester

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Technology Process of 3-{(2R,3S)-1-(4-Nitro-benzyloxycarbonylmethyl)-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid phenyl ester

There total 7 articles about 3-{(2R,3S)-1-(4-Nitro-benzyloxycarbonylmethyl)-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid phenyl ester 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: 81.0%

: 619-73-8
4-nitrobenzyl chloride

: 140866-87-1
3-{(2R,3S)-4-Oxo-1-phenoxycarbonylmethyl-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid phenyl ester

: 140866-88-2
3-{(2R,3S)-1-(4-Nitro-benzyloxycarbonylmethyl)-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid phenyl ester

Guidance literature:: With potassium p-nitrobenzyloxide; In tetrahydrofuran; at 12 ℃; for 1.16667h;
DOI:10.1016/S0040-4039(00)91559-4

Reference yield:

: 140866-85-9
(2S,3R)-3-[(E)-tert-Butoxycarbonylmethylimino-methyl]-oxirane-2-carboxylic acid ethyl ester

: 140866-88-2
3-{(2R,3S)-1-(4-Nitro-benzyloxycarbonylmethyl)-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid phenyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 60 percent / NEt₃ / CH₂Cl₂ / 1) -78 deg C, 20 min, 2) -20 deg C, 16 h

2: NaI, TsOH / acetonitrile / 2 h / 3 °C

3: H₂ / 5percent Pd-C / ethanol / 2.5 h / 25 °C

4: TFA / CH₂Cl₂ / 24 h / -15 °C

5: tetrahydrofuran / 2 h / 25 °C

6: aq. NaOH / tetrahydrofuran / 4 h / 25 °C

7: 80 percent / DCC, DMAP / CH₂Cl₂; dimethylformamide

8: 81 percent / potassium p-nitrobenzyloxide / tetrahydrofuran / 1.17 h / 12 °C

With dmap; sodium hydroxide; potassium p-nitrobenzyloxide; hydrogen; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(00)91559-4

Reference yield:

: 140925-22-0
(E)-3-[(2R,3S)-1-tert-Butoxycarbonylmethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-2-yl]-acrylic acid ethyl ester

: 140866-88-2
3-{(2R,3S)-1-(4-Nitro-benzyloxycarbonylmethyl)-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid phenyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: H₂ / 5percent Pd-C / ethanol / 2.5 h / 25 °C

2: TFA / CH₂Cl₂ / 24 h / -15 °C

3: tetrahydrofuran / 2 h / 25 °C

4: aq. NaOH / tetrahydrofuran / 4 h / 25 °C

5: 80 percent / DCC, DMAP / CH₂Cl₂; dimethylformamide

6: 81 percent / potassium p-nitrobenzyloxide / tetrahydrofuran / 1.17 h / 12 °C

With dmap; sodium hydroxide; potassium p-nitrobenzyloxide; hydrogen; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)91559-4