{(3E)-4-[N-((1R)-1-{N-[(1R)-1-benzyl-2-((3S)-3-((dimethylamino)methyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-methylcarbamoyl]-1,1-dimethylbut-3-enyl}carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(3E)-4-[N-((1R)-1-{N-[(1R)-1-benzyl-2-((3S)-3-((dimethylamino)methyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-methylcarbamoyl]-1,1-dimethylbut-3-enyl}carbamic acid tert-butyl ester
• CAS No.: 254905-70-9
• Molecular Formula: C₄₄H₆₁N₅O₅
• Molecular Weight: 739.999
• Mol file: 254905-70-9.mol

Synonyms:{(3E)-4-[N-((1R)-1-{N-[(1R)-1-benzyl-2-((3S)-3-((dimethylamino)methyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-methylcarbamoyl]-1,1-dimethylbut-3-enyl}carbamic acid tert-butyl ester

Chemical Property of {(3E)-4-[N-((1R)-1-{N-[(1R)-1-benzyl-2-((3S)-3-((dimethylamino)methyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-methylcarbamoyl]-1,1-dimethylbut-3-enyl}carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(3E)-4-[N-((1R)-1-{N-[(1R)-1-benzyl-2-((3S)-3-((dimethylamino)methyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-methylcarbamoyl]-1,1-dimethylbut-3-enyl}carbamic acid tert-butyl ester

There total 8 articles about {(3E)-4-[N-((1R)-1-{N-[(1R)-1-benzyl-2-((3S)-3-((dimethylamino)methyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-methylcarbamoyl]-1,1-dimethylbut-3-enyl}carbamic acid tert-butyl 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:

N-tert-butoxycarbonyl-N-methyl-D-phenylalanine (37553-65-4,64263-83-8,85466-66-6) → {(3E)-4-[N-((1R)-1-{N-[(1R)-1-benzyl-2-((3S)-3-((dimethylamino)methyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-methylcarbamoyl]-1,1-dimethylbut-3-enyl}carbamic acid tert-butyl ester (254905-70-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: HOAt; EDAC*HCl / CH₂Cl₂; dimethylformamide / 0.33 h / 0 °C

1.2: 1.69 g / iPr₂NEt / CH₂Cl₂; dimethylformamide / 72 h / 0 - 20 °C

2.1: 1.15 g / trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 0 °C

3.1: HOAt; EDAC*HCl / CH₂Cl₂; dimethylformamide / 0.33 h / 0 °C

3.2: 1.18 g / iPr₂NEt / CH₂Cl₂; dimethylformamide / 72 h / 0 - 20 °C

4.1: 788 mg / trifluoroacetic acid / CH₂Cl₂ / 0.83 h / 0 °C

5.1: HOAt; EDAC*HCl / CH₂Cl₂ / 0.33 h / 0 °C

5.2: 398 mg / iPr₂NEt / CH₂Cl₂; dimethylformamide / 16 h / 0 - 20 °C

With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0223-5234(02)01370-3

Reference yield:

(3R)-3-formylpiperidine-1-carboxylic acid tert-butyl ester (194726-46-0) → {(3E)-4-[N-((1R)-1-{N-[(1R)-1-benzyl-2-((3S)-3-((dimethylamino)methyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-methylcarbamoyl]-1,1-dimethylbut-3-enyl}carbamic acid tert-butyl ester (254905-70-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 866 mg / NaB(OAc)3H; AcOH; molecular sieves / CH₂Cl₂; ethanol / 16 h / 20 °C

2.1: HCl / ethyl acetate / 0.75 h / 20 °C

3.1: HOAt; EDAC*HCl / CH₂Cl₂; dimethylformamide / 0.33 h / 0 °C

3.2: 1.69 g / iPr₂NEt / CH₂Cl₂; dimethylformamide / 72 h / 0 - 20 °C

4.1: 1.15 g / trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 0 °C

5.1: HOAt; EDAC*HCl / CH₂Cl₂; dimethylformamide / 0.33 h / 0 °C

5.2: 1.18 g / iPr₂NEt / CH₂Cl₂; dimethylformamide / 72 h / 0 - 20 °C

6.1: 788 mg / trifluoroacetic acid / CH₂Cl₂ / 0.83 h / 0 °C

7.1: HOAt; EDAC*HCl / CH₂Cl₂ / 0.33 h / 0 °C

7.2: 398 mg / iPr₂NEt / CH₂Cl₂; dimethylformamide / 16 h / 0 - 20 °C

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; molecular sieve; sodium tris(acetoxy)borohydride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0223-5234(02)01370-3

Reference yield:

(3S)-3-(dimethylaminomethyl)piperidine-1-carboxylic acid tert-butyl ester (254905-64-1,1002359-82-1) → {(3E)-4-[N-((1R)-1-{N-[(1R)-1-benzyl-2-((3S)-3-((dimethylamino)methyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-methylcarbamoyl]-1,1-dimethylbut-3-enyl}carbamic acid tert-butyl ester (254905-70-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: HCl / ethyl acetate / 0.75 h / 20 °C

2.1: HOAt; EDAC*HCl / CH₂Cl₂; dimethylformamide / 0.33 h / 0 °C

2.2: 1.69 g / iPr₂NEt / CH₂Cl₂; dimethylformamide / 72 h / 0 - 20 °C

3.1: 1.15 g / trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 0 °C

4.1: HOAt; EDAC*HCl / CH₂Cl₂; dimethylformamide / 0.33 h / 0 °C

4.2: 1.18 g / iPr₂NEt / CH₂Cl₂; dimethylformamide / 72 h / 0 - 20 °C

5.1: 788 mg / trifluoroacetic acid / CH₂Cl₂ / 0.83 h / 0 °C

6.1: HOAt; EDAC*HCl / CH₂Cl₂ / 0.33 h / 0 °C

6.2: 398 mg / iPr₂NEt / CH₂Cl₂; dimethylformamide / 16 h / 0 - 20 °C

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0223-5234(02)01370-3

upstream raw materials:

N-tert-butoxycarbonyl-N-methyl-D-phenylalanine

(3R)-3-formylpiperidine-1-carboxylic acid tert-butyl ester

(3S)-3-(dimethylaminomethyl)piperidine-1-carboxylic acid tert-butyl ester

(3R)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester