tert-butyl (2R,5S)-2-[(R)-hydroxy(pyridin-3-yl)methyl]-5-(4-{[(2-oxopyrrolidin-1-yl)acetyl]amino}benzyl)pyrrolidine-1-carboxylate trifluoroacetate

Base Information

• Chemical Name: tert-butyl (2R,5S)-2-[(R)-hydroxy(pyridin-3-yl)methyl]-5-(4-{[(2-oxopyrrolidin-1-yl)acetyl]amino}benzyl)pyrrolidine-1-carboxylate trifluoroacetate
• CAS No.: 1190615-41-8
• Molecular Formula: C₂HF₃O₂*C₂₈H₃₆N₄O₅
• Molecular Weight: 622.642
• Mol file: 1190615-41-8.mol

Synonyms:tert-butyl (2R,5S)-2-[(R)-hydroxy(pyridin-3-yl)methyl]-5-(4-{[(2-oxopyrrolidin-1-yl)acetyl]amino}benzyl)pyrrolidine-1-carboxylate trifluoroacetate

Chemical Property of tert-butyl (2R,5S)-2-[(R)-hydroxy(pyridin-3-yl)methyl]-5-(4-{[(2-oxopyrrolidin-1-yl)acetyl]amino}benzyl)pyrrolidine-1-carboxylate trifluoroacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2R,5S)-2-[(R)-hydroxy(pyridin-3-yl)methyl]-5-(4-{[(2-oxopyrrolidin-1-yl)acetyl]amino}benzyl)pyrrolidine-1-carboxylate trifluoroacetate

There total 13 articles about tert-butyl (2R,5S)-2-[(R)-hydroxy(pyridin-3-yl)methyl]-5-(4-{[(2-oxopyrrolidin-1-yl)acetyl]amino}benzyl)pyrrolidine-1-carboxylate trifluoroacetate 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: 75.0%

(2S,5R)-tert-butyl 2-(4-aminobenzyl)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate (1190615-16-7) + N-(2-pyrrolidone)-2-acetic acid (53934-76-2) + trifluoroacetic acid (76-05-1) → tert-butyl (2R,5S)-2-[(R)-hydroxy(pyridin-3-yl)methyl]-5-(4-{[(2-oxopyrrolidin-1-yl)acetyl]amino}benzyl)pyrrolidine-1-carboxylate trifluoroacetate (1190615-41-8)

Guidance literature:

(2S,5R)-tert-butyl 2-(4-aminobenzyl)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate; N-(2-pyrrolidone)-2-acetic acid; With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

trifluoroacetic acid; In water; acetonitrile; HPLC;

Reference yield:

6-chloronicotinylaldehyde (23100-12-1) → tert-butyl (2R,5S)-2-[(R)-hydroxy(pyridin-3-yl)methyl]-5-(4-{[(2-oxopyrrolidin-1-yl)acetyl]amino}benzyl)pyrrolidine-1-carboxylate trifluoroacetate (1190615-41-8)

Guidance literature:

Multi-step reaction with 13 steps

1.1: chloro-trimethyl-silane; triethylamine; magnesium chloride / ethyl acetate / 72 h / 20 °C

2.1: trifluoroacetic acid / methanol / 5 h / 20 °C

3.1: 2,6-dimethylpyridine / dichloromethane / 0 - 3 °C

4.1: water; dihydrogen peroxide; sodium hydroxide / tetrahydrofuran / 0 - 5 °C

4.2: 15 °C

4.3: 0 °C / pH 3

5.1: diphenyl phosphoryl azide; triethylamine / toluene / 6 h / 20 °C

5.2: 16 h / 100 °C

6.1: triethylamine / copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / acetonitrile / 15 h / 20 °C

7.1: pyrrolidine / N,N-dimethyl-formamide / 5 h / 80 °C

7.2: 3 h / 20 °C

8.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

9.1: methanol; sodium cyanoborohydride / 0 °C

10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C

11.1: hydrogen; potassium acetate / palladium 10% on activated carbon / ethanol / 8 h / 2585.81 Torr

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h

13.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 24 h / 20 °C

13.2: HPLC

With pyrrolidine; 2,6-dimethylpyridine; methanol; chloro-trimethyl-silane; 1-hydroxy-7-aza-benzotriazole; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; potassium acetate; sodium cyanoborohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; magnesium chloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

(R)-2-((S)-(6-chloropyridin-3-yl)((trimethylsilyl)oxy)methyl)hex-5-ynoic acid (1190614-98-2) → tert-butyl (2R,5S)-2-[(R)-hydroxy(pyridin-3-yl)methyl]-5-(4-{[(2-oxopyrrolidin-1-yl)acetyl]amino}benzyl)pyrrolidine-1-carboxylate trifluoroacetate (1190615-41-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: diphenyl phosphoryl azide; triethylamine / toluene / 6 h / 20 °C

1.2: 16 h / 100 °C

2.1: triethylamine / copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / acetonitrile / 15 h / 20 °C

3.1: pyrrolidine / N,N-dimethyl-formamide / 5 h / 80 °C

3.2: 3 h / 20 °C

4.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

5.1: methanol; sodium cyanoborohydride / 0 °C

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C

7.1: hydrogen; potassium acetate / palladium 10% on activated carbon / ethanol / 8 h / 2585.81 Torr

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h

9.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 24 h / 20 °C

9.2: HPLC

With pyrrolidine; methanol; 1-hydroxy-7-aza-benzotriazole; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; hydrogen; potassium acetate; sodium cyanoborohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

(2S,5R)-tert-butyl 2-(4-aminobenzyl)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidine-1-carboxylate

N-(2-pyrrolidone)-2-acetic acid

trifluoroacetic acid

6-chloronicotinylaldehyde