N-[(2S,3R)-2-(acetylamino)-3-hydroxybutanoyl]-N-{(2S)-2-[benzyl(methyl)amino]-3-phenylpropanoyl}-1-formyl-D-tryptophanamide

Base Information

• Chemical Name: N-[(2S,3R)-2-(acetylamino)-3-hydroxybutanoyl]-N-{(2S)-2-[benzyl(methyl)amino]-3-phenylpropanoyl}-1-formyl-D-tryptophanamide
• CAS No.: 126088-92-4
• Molecular Formula: C35H39 N5 O6
• Molecular Weight: 625.7141
• Mol file: 126088-92-4.mol

Synonyms:FR 113680;R 544

Chemical Property of N-[(2S,3R)-2-(acetylamino)-3-hydroxybutanoyl]-N-{(2S)-2-[benzyl(methyl)amino]-3-phenylpropanoyl}-1-formyl-D-tryptophanamide

Chemical Property:

• Density: 1.26g/cm³

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-[(2S,3R)-2-(acetylamino)-3-hydroxybutanoyl]-N-{(2S)-2-[benzyl(methyl)amino]-3-phenylpropanoyl}-1-formyl-D-tryptophanamide

There total 10 articles about N-[(2S,3R)-2-(acetylamino)-3-hydroxybutanoyl]-N-{(2S)-2-[benzyl(methyl)amino]-3-phenylpropanoyl}-1-formyl-D-tryptophanamide 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: 82.4%

acetic anhydride (108-24-7) + H-Thr-D-Trp(CHO)-Phe-NMeBzl*HCl (126088-90-2) → FR 113680 (126088-92-4)

Guidance literature:

With triethylamine; In dichloromethane; at -15 ℃; for 0.333333h;

DOI:10.1021/jm00095a013

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → FR 113680 (126088-92-4)

Guidance literature:

Multi-step reaction with 8 steps

1: N-methylmorpholine / CH₂Cl₂ / 0.33 h / -20 °C

2: CH₂Cl₂ / 2 h / -35 - 0 °C

3: 85.4 percent / anisole, HCl / dioxane; CH₂Cl₂ / 1.25 h / 0 - 20 °C

4: 86.7 percent / HOBT, 1-ethyl-3-<3-(N,N-dimethylamino)propyl>carbodiimide (WSCD) / dimethylformamide / 3 h / 0 - 20 °C

5: HCl / dioxane; CH₂Cl₂ / 1.17 h / 0 - 20 °C

6: 94.7 percent / HOBT, 1-ethyl-3-<3-(N,N-dimethylamino)propyl>carbodiimide (WSCD) / dimethylformamide / 3.5 h / 0 - 20 °C

7: 100 percent / HCl / CH₂Cl₂; dioxane / 1.17 h / 0 - 20 °C

8: 82.4 percent / Et₃N / CH₂Cl₂ / 0.33 h / -15 °C

With 4-methyl-morpholine; hydrogenchloride; benzotriazol-1-ol; methoxybenzene; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00095a013

Reference yield:

Boc-Phe-O-COO-isoBu (67729-36-6,60398-40-5) → FR 113680 (126088-92-4)

Guidance literature:

Multi-step reaction with 7 steps

1: CH₂Cl₂ / 2 h / -35 - 0 °C

2: 85.4 percent / anisole, HCl / dioxane; CH₂Cl₂ / 1.25 h / 0 - 20 °C

3: 86.7 percent / HOBT, 1-ethyl-3-<3-(N,N-dimethylamino)propyl>carbodiimide (WSCD) / dimethylformamide / 3 h / 0 - 20 °C

4: HCl / dioxane; CH₂Cl₂ / 1.17 h / 0 - 20 °C

5: 94.7 percent / HOBT, 1-ethyl-3-<3-(N,N-dimethylamino)propyl>carbodiimide (WSCD) / dimethylformamide / 3.5 h / 0 - 20 °C

6: 100 percent / HCl / CH₂Cl₂; dioxane / 1.17 h / 0 - 20 °C

7: 82.4 percent / Et₃N / CH₂Cl₂ / 0.33 h / -15 °C

With hydrogenchloride; benzotriazol-1-ol; methoxybenzene; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00095a013

upstream raw materials:

acetic anhydride

H-Thr-D-Trp(CHO)-Phe-NMeBzl*HCl

N-tert-butoxycarbonyl-L-phenylalanine

Boc-Phe-O-COO-isoBu