(2S,3S,4S)-N-(benzyloxycarbonyl)-2-carboxy-4-(1-methylethenyl)pyrrolidine-3-acetic acid

Base Information

• Chemical Name: (2S,3S,4S)-N-(benzyloxycarbonyl)-2-carboxy-4-(1-methylethenyl)pyrrolidine-3-acetic acid
• CAS No.: 73903-33-0
• Molecular Formula: C₁₈H₂₁NO₆
• Molecular Weight: 347.368
• Mol file: 73903-33-0.mol

Synonyms:(2S,3S,4S)-N-(benzyloxycarbonyl)-2-carboxy-4-(1-methylethenyl)pyrrolidine-3-acetic acid

Chemical Property of (2S,3S,4S)-N-(benzyloxycarbonyl)-2-carboxy-4-(1-methylethenyl)pyrrolidine-3-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-N-(benzyloxycarbonyl)-2-carboxy-4-(1-methylethenyl)pyrrolidine-3-acetic acid

There total 37 articles about (2S,3S,4S)-N-(benzyloxycarbonyl)-2-carboxy-4-(1-methylethenyl)pyrrolidine-3-acetic 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: 80.0%

(-)-kainic acid (487-79-6) + benzyl chloroformate (501-53-1,94274-21-2) → (2S,3S,4S)-N-(benzyloxycarbonyl)-2-carboxy-4-(1-methylethenyl)pyrrolidine-3-acetic acid (73903-33-0)

Guidance literature:

With potassium hydroxide; sodium carbonate; In water; for 16h; Ambient temperature;

DOI:10.1002/hlca.19950780502

Reference yield:

((R)-2-Benzyloxy-1-formyl-ethyl)-(3-methyl-but-2-enyl)-carbamic acid benzyl ester (115890-38-5) → (2S,3S,4S)-N-(benzyloxycarbonyl)-2-carboxy-4-(1-methylethenyl)pyrrolidine-3-acetic acid (73903-33-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 4.24 g / ethylenediammonium diacetate / propan-2-ol / 16 h / Ambient temperature

2: 2.27 g / H₂O / dioxane / 15 h / Heating

3: 41 percent / BBr₃ / CH₂Cl₂ / 1.) -40 deg C to 0 deg C, 1 h, 2.) 0 deg C, 30 min

4: 83 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 25 h / Ambient temperature

5: 97 percent / NaBH₄ / propan-2-ol / 0.67 h / Heating

6: 85 percent / 2 h / 270 °C

7: 51 mg / K₂CO₃, methanol / 1 h / Ambient temperature

8: 35.8 mg / 1 N n-Bu₄NF / tetrahydrofuran / 0.67 h / Ambient temperature

9: 34 mg / 8 N Jones reagent / acetone / 0.08 h / 0 °C

With methanol; dmap; sodium tetrahydroborate; jones reagent; tetrabutyl ammonium fluoride; water; boron tribromide; potassium carbonate; ethylenediamine diacetic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; isopropyl alcohol; acetone;

DOI:10.1021/ja00227a029

Reference yield:

(2R,3RS)-2-<(benzyloxycarbonyl)prenylamino>-1-(benzyloxy)-3,4-butandiol → (2S,3S,4S)-N-(benzyloxycarbonyl)-2-carboxy-4-(1-methylethenyl)pyrrolidine-3-acetic acid (73903-33-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 3.27 g / NaIO₄ / methanol; H₂O / 2 h / 0 °C

2: 4.24 g / ethylenediammonium diacetate / propan-2-ol / 16 h / Ambient temperature

3: 2.27 g / H₂O / dioxane / 15 h / Heating

4: 41 percent / BBr₃ / CH₂Cl₂ / 1.) -40 deg C to 0 deg C, 1 h, 2.) 0 deg C, 30 min

5: 83 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 25 h / Ambient temperature

6: 97 percent / NaBH₄ / propan-2-ol / 0.67 h / Heating

7: 85 percent / 2 h / 270 °C

8: 51 mg / K₂CO₃, methanol / 1 h / Ambient temperature

9: 35.8 mg / 1 N n-Bu₄NF / tetrahydrofuran / 0.67 h / Ambient temperature

10: 34 mg / 8 N Jones reagent / acetone / 0.08 h / 0 °C

With methanol; dmap; sodium tetrahydroborate; sodium periodate; jones reagent; tetrabutyl ammonium fluoride; water; boron tribromide; potassium carbonate; ethylenediamine diacetic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; isopropyl alcohol; acetone;

DOI:10.1021/ja00227a029

upstream raw materials:

(-)-kainic acid

benzyl chloroformate

(2S,3S,4S)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isopropenylpyrrolidine

1-(benzyloxycarbonyl)kainic acid dimethyl ester

Downstream raw materials:

(2S,3S,4S)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isopropenylpyrrolidine

(-)-kainic acid

1-(benzyloxycarbonyl)kainic acid dimethyl ester