(4S,5S)-4-Carboxymethyl-5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-oxazolidine-3-carboxylic acid cyclohexyl ester

Base Information

• Chemical Name: (4S,5S)-4-Carboxymethyl-5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-oxazolidine-3-carboxylic acid cyclohexyl ester
• CAS No.: 118972-89-7
• Molecular Formula: C₂₂H₂₆N₂O₇
• Molecular Weight: 430.458
• Mol file: 118972-89-7.mol

Synonyms:

Chemical Property of (4S,5S)-4-Carboxymethyl-5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-oxazolidine-3-carboxylic acid cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-Carboxymethyl-5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-oxazolidine-3-carboxylic acid cyclohexyl ester

There total 8 articles about (4S,5S)-4-Carboxymethyl-5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-oxazolidine-3-carboxylic acid cyclohexyl 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: 95.0%

(4S,5S)-5-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-4-(2-hydroxy-ethyl)-oxazolidine-3-carboxylic acid cyclohexyl ester (118972-88-6) → (4S,5S)-4-Carboxymethyl-5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-oxazolidine-3-carboxylic acid cyclohexyl ester (118972-89-7)

Guidance literature:

With jones' reagent;

DOI:10.1016/S0040-4039(00)82116-4

Reference yield:

N-(3-butenyl)phthalimide (52898-32-5) → (4S,5S)-4-Carboxymethyl-5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-oxazolidine-3-carboxylic acid cyclohexyl ester (118972-89-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) O₃; 2) dimethyl sulfide, sodium acetate / 1) MeOH, CH₂Cl₂, -78 deg C;

2: 56 percent / tetrahydrofuran / -78 °C

3: 69 percent / TsOH / diethyl ether

4: 93 percent / H₂ / 2 weightpercent Pd/BaSO₄, 10 weightpercent quinoline / methanol / 4 h / 1551.4 Torr

5: 1) mercuric trifluoroacetate, sodium bicarbonate; 2) 5percent NaOH, sodium borohydride / 1) ethyl acetate;

6: 67 percent / formic acid (10 volume percent) / Pd/C / methanol

7: 95 percent / Jones' reagent

With sodium hydroxide; sodium tetrahydroborate; formic acid; jones' reagent; dimethylsulfide; hydrogen; sodium acetate; mercury(II) trifluoroacetate; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; quinoline; palladium on activated charcoal; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1016/S0040-4039(00)82116-4

Reference yield:

3-(N-phthaloyl)propionaldehyde (2436-29-5) → (4S,5S)-4-Carboxymethyl-5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-oxazolidine-3-carboxylic acid cyclohexyl ester (118972-89-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 56 percent / tetrahydrofuran / -78 °C

2: 69 percent / TsOH / diethyl ether

3: 93 percent / H₂ / 2 weightpercent Pd/BaSO₄, 10 weightpercent quinoline / methanol / 4 h / 1551.4 Torr

4: 1) mercuric trifluoroacetate, sodium bicarbonate; 2) 5percent NaOH, sodium borohydride / 1) ethyl acetate;

5: 67 percent / formic acid (10 volume percent) / Pd/C / methanol

6: 95 percent / Jones' reagent

With sodium hydroxide; sodium tetrahydroborate; formic acid; jones' reagent; hydrogen; mercury(II) trifluoroacetate; sodium hydrogencarbonate; toluene-4-sulfonic acid; quinoline; palladium on activated charcoal; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1016/S0040-4039(00)82116-4

upstream raw materials:

(4S,5S)-5-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-4-(2-hydroxy-ethyl)-oxazolidine-3-carboxylic acid cyclohexyl ester

N-(3-butenyl)phthalimide

3-(N-phthaloyl)propionaldehyde

2-(6-Benzyloxy-3-hydroxy-hex-4-ynyl)-isoindole-1,3-dione