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

Base Information

• Chemical Name: 3-{(2R,3S)-1-Carboxymethyl-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid ethyl ester; compound with pyrrolidine
• CAS No.: 135693-13-9
• Molecular Formula: C₄H₉N*C₂₂H₂₇N₃O₇
• Molecular Weight: 516.594
• Mol file: 135693-13-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 3-{(2R,3S)-1-Carboxymethyl-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid ethyl ester; compound with pyrrolidine 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: 90.0%

pyrrolidine (123-75-1) + 3-[(2R,3S)-1-Carboxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-2-yl]-propionic acid ethyl ester (135693-14-0) → 3-{(2R,3S)-1-Carboxymethyl-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid ethyl ester; compound with pyrrolidine (135693-13-9)

Guidance literature:

In tetrahydrofuran; at 25 ℃;

DOI:10.1016/S0040-4039(00)92691-1

Reference yield:

(2S,3R)-2,3-epoxy-4-hydroxybutanoic acid ethyl ester (136171-94-3) → 3-{(2R,3S)-1-Carboxymethyl-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid ethyl ester; compound with pyrrolidine (135693-13-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) (COCl)2, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 30 min

2: MgSO₄ / CH₂Cl₂ / 14 h / -26 °C

3: 60 percent / NEt₃ / CH₂Cl₂ / 1) -78 deg C, 20 min, 2) -20 deg C, 16 h

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

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

6: TFA / CH₂Cl₂ / 24 h / -15 °C

7: tetrahydrofuran / 2 h / 25 °C

With oxalyl dichloride; hydrogen; magnesium sulfate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)91559-4

Reference yield:

(2S,3S)-3-formyloxirane-2-carboxylic acid ethyl ester (140925-20-8) → 3-{(2R,3S)-1-Carboxymethyl-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid ethyl ester; compound with pyrrolidine (135693-13-9)

Guidance literature:

Multi-step reaction with 6 steps

1: MgSO₄ / CH₂Cl₂ / 14 h / -26 °C

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

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

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

5: TFA / CH₂Cl₂ / 24 h / -15 °C

6: tetrahydrofuran / 2 h / 25 °C

With hydrogen; magnesium sulfate; 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

upstream raw materials:

pyrrolidine

3-[(2R,3S)-1-Carboxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-2-yl]-propionic acid ethyl ester

3-[(2R,3S)-1-tert-Butoxycarbonylmethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-2-yl]-propionic acid ethyl ester

(2S,3R)-2,3-epoxy-4-hydroxybutanoic acid ethyl ester

Downstream raw materials:

(6R,7S)-3-Chloro-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(6R*,7S*)-3-chloro-7-amino-8-oxo-1-azabicyclo<4.2.0>oct-2-en-2-carboxylic acid

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