L-Prolinamide, (4R)-4-hydroxy-L-prolyl-L-glutaminyl-2-methylalanyl-(4R)-4-hydroxy-L-prol yl-2-methylalanyl-N-[(1S)-1-(hydroxymethyl)-2-phenylethyl]-

Base Information

• Chemical Name: L-Prolinamide, (4R)-4-hydroxy-L-prolyl-L-glutaminyl-2-methylalanyl-(4R)-4-hydroxy-L-prol yl-2-methylalanyl-N-[(1S)-1-(hydroxymethyl)-2-phenylethyl]-
• CAS No.: 193007-44-2
• Molecular Formula: C₃₇H₅₆N₈O₁₀
• Molecular Weight: 772.899
• Mol file: 193007-44-2.mol

Synonyms:

Chemical Property of L-Prolinamide, (4R)-4-hydroxy-L-prolyl-L-glutaminyl-2-methylalanyl-(4R)-4-hydroxy-L-prol yl-2-methylalanyl-N-[(1S)-1-(hydroxymethyl)-2-phenylethyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Prolinamide, (4R)-4-hydroxy-L-prolyl-L-glutaminyl-2-methylalanyl-(4R)-4-hydroxy-L-prol yl-2-methylalanyl-N-[(1S)-1-(hydroxymethyl)-2-phenylethyl]-

There total 14 articles about L-Prolinamide, (4R)-4-hydroxy-L-prolyl-L-glutaminyl-2-methylalanyl-(4R)-4-hydroxy-L-prol yl-2-methylalanyl-N-[(1S)-1-(hydroxymethyl)-2-phenylethyl]- 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:

C52H66N8O12 (193007-24-8) → 2-[(4-hydroxy-pyrrolidine-2-carbonyl)-amino]-pentanedioic acid 5-amide 1-{[2-(4-hydroxy-2-{2-[2-(1-hydroxymethyl-2-phenyl-ethylcarbamoyl)-pyrrolidin-1-yl]-1,1-dimethyl-2-oxo-ethylcarbamoyl}-pyrrolidin-1-yl)-1,1-dimethyl-2-oxo-ethyl]-amide} (193007-44-2)

Guidance literature:

With diethylamine; In N,N-dimethyl-formamide; for 0.5h;

Reference yield:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → 2-[(4-hydroxy-pyrrolidine-2-carbonyl)-amino]-pentanedioic acid 5-amide 1-{[2-(4-hydroxy-2-{2-[2-(1-hydroxymethyl-2-phenyl-ethylcarbamoyl)-pyrrolidin-1-yl]-1,1-dimethyl-2-oxo-ethylcarbamoyl}-pyrrolidin-1-yl)-1,1-dimethyl-2-oxo-ethyl]-amide} (193007-44-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 92 percent / benzotriazol-1-yloxy-tris(Me₂N)phosphonium⁽¹⁺⁾*PF₆^(1-); DIPEA / dimethylformamide / 0.67 h

2.1: TFA / CHCl₃ / 0.33 h / 20 °C

3.1: benzotriazol-1-yloxy-tris(Me₂N)phosphonium⁽¹⁺⁾*PF₆^(1-); DMAP / dimethylformamide / 0.17 h

3.2: 444 mg / DIPEA / dimethylformamide / 0.5 h

4.1: NaOH / dioxane; methanol; H₂O / 0.07 h

5.1: 330 mg / benzotriazol-1-yloxy-tris(Me₂N)phosphonium⁽¹⁺⁾*PF₆^(1-); DIPEA / dimethylformamide / 0.67 h

6.1: NaOH / dioxane; methanol; H₂O

7.1: benzotriazol-1-yloxy-tris(Me₂N)phosphonium⁽¹⁺⁾*PF₆^(1-); DMAP / dimethylformamide / 0.17 h

7.2: 120 mg / DIPEA / dimethylformamide / 0.5 h

8.1: NaOH / dioxane; methanol; H₂O

9.1: 83 mg / benzotriazol-1-yloxy-tris(Me₂N)phosphonium⁽¹⁺⁾*PF₆^(1-); DIPEA / dimethylformamide

10.1: NaOH / dioxane; methanol; H₂O

11.1: 41 mg / benzotriazol-1-yloxy-tris(Me₂N)phosphonium⁽¹⁺⁾*PF₆^(1-); DIPEA / dimethylformamide

12.1: TFA / CH₂Cl₂ / 0.33 h / 20 °C

13.1: 18 mg / diethylamine / dimethylformamide / 0.5 h

With dmap; sodium hydroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In 1,4-dioxane; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide;

Reference yield:

L-Phenylalaninol (3182-95-4) → 2-[(4-hydroxy-pyrrolidine-2-carbonyl)-amino]-pentanedioic acid 5-amide 1-{[2-(4-hydroxy-2-{2-[2-(1-hydroxymethyl-2-phenyl-ethylcarbamoyl)-pyrrolidin-1-yl]-1,1-dimethyl-2-oxo-ethylcarbamoyl}-pyrrolidin-1-yl)-1,1-dimethyl-2-oxo-ethyl]-amide} (193007-44-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 92 percent / benzotriazol-1-yloxy-tris(Me₂N)phosphonium⁽¹⁺⁾*PF₆^(1-); DIPEA / dimethylformamide / 0.67 h

2.1: TFA / CHCl₃ / 0.33 h / 20 °C

3.1: benzotriazol-1-yloxy-tris(Me₂N)phosphonium⁽¹⁺⁾*PF₆^(1-); DMAP / dimethylformamide / 0.17 h

3.2: 444 mg / DIPEA / dimethylformamide / 0.5 h

4.1: NaOH / dioxane; methanol; H₂O / 0.07 h

5.1: 330 mg / benzotriazol-1-yloxy-tris(Me₂N)phosphonium⁽¹⁺⁾*PF₆^(1-); DIPEA / dimethylformamide / 0.67 h

6.1: NaOH / dioxane; methanol; H₂O

7.1: benzotriazol-1-yloxy-tris(Me₂N)phosphonium⁽¹⁺⁾*PF₆^(1-); DMAP / dimethylformamide / 0.17 h

7.2: 120 mg / DIPEA / dimethylformamide / 0.5 h

8.1: NaOH / dioxane; methanol; H₂O

9.1: 83 mg / benzotriazol-1-yloxy-tris(Me₂N)phosphonium⁽¹⁺⁾*PF₆^(1-); DIPEA / dimethylformamide

10.1: NaOH / dioxane; methanol; H₂O

11.1: 41 mg / benzotriazol-1-yloxy-tris(Me₂N)phosphonium⁽¹⁺⁾*PF₆^(1-); DIPEA / dimethylformamide

12.1: TFA / CH₂Cl₂ / 0.33 h / 20 °C

13.1: 18 mg / diethylamine / dimethylformamide / 0.5 h

With dmap; sodium hydroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In 1,4-dioxane; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide;

upstream raw materials:

C₅₂H₆₆N₈O₁₂

1-(tert-butoxycarbonyl)-L-proline

L-Phenylalaninol

(S)-tert-butyl 2-((S)-1-hydroxy-3-phenylpropan-2-ylcarbamoyl)pyrrolidine-1-carboxylate