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

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Chemical Name:3-{(2R,3S)-1-Carboxymethyl-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid
CAS No.:140866-86-0
Molecular Formula:C₂₀H₂₃N₃O₇
Molecular Weight:417.419
Hs Code.:

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

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

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

There total 6 articles about 3-{(2R,3S)-1-Carboxymethyl-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid 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:

: 135693-13-9
3-{(2R,3S)-1-Carboxymethyl-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid ethyl ester; compound with pyrrolidine

: 140866-86-0
3-{(2R,3S)-1-Carboxymethyl-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; at 25 ℃; for 4h; Yield given;
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

: 140866-86-0
3-{(2R,3S)-1-Carboxymethyl-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid

Guidance literature:: Multi-step reaction with 6 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

With sodium hydroxide; hydrogen; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; 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

: 140866-86-0
3-{(2R,3S)-1-Carboxymethyl-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid

Guidance literature:: Multi-step reaction with 4 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

With sodium hydroxide; hydrogen; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1016/S0040-4039(00)91559-4