N-(isobutoxycarbonyl)-L-valyl-N¹-{(1S)-1-[({2-[2-chloro-4-(methoxycarbonyl)phenyl]ethyl}-amino)carbonyl]-3,3-difluoropropyl}-L-leucinamide

Base Information

• Chemical Name: N-(isobutoxycarbonyl)-L-valyl-N¹-{(1S)-1-[({2-[2-chloro-4-(methoxycarbonyl)phenyl]ethyl}-amino)carbonyl]-3,3-difluoropropyl}-L-leucinamide
• CAS No.: 484649-01-6
• Molecular Formula: C₃₀H₄₅ClF₂N₄O₇
• Molecular Weight: 647.16

Synonyms:N-(isobutoxycarbonyl)-L-valyl-N¹-{(1S)-1-[({2-[2-chloro-4-(methoxycarbonyl)phenyl]ethyl}-amino)carbonyl]-3,3-difluoropropyl}-L-leucinamide

Chemical Property of N-(isobutoxycarbonyl)-L-valyl-N¹-{(1S)-1-[({2-[2-chloro-4-(methoxycarbonyl)phenyl]ethyl}-amino)carbonyl]-3,3-difluoropropyl}-L-leucinamide

Chemical Property:

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Technology Process of N-(isobutoxycarbonyl)-L-valyl-N¹-{(1S)-1-[({2-[2-chloro-4-(methoxycarbonyl)phenyl]ethyl}-amino)carbonyl]-3,3-difluoropropyl}-L-leucinamide

There total 8 articles about N-(isobutoxycarbonyl)-L-valyl-N¹-{(1S)-1-[({2-[2-chloro-4-(methoxycarbonyl)phenyl]ethyl}-amino)carbonyl]-3,3-difluoropropyl}-L-leucinamide 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: 90.0%

L-valyl-N1-{(1S)-1-[({2-[2-chloro-4-(methoxycarbonyl)-phenyl]ethyl}amino)carbonyl]-3,3-difluoropropyl}-L-leucinamide + isobutyl chloroformate (543-27-1) → N-(isobutoxycarbonyl)-L-valyl-N1-{(1S)-1-[({2-[2-chloro-4-(methoxycarbonyl)phenyl]ethyl}-amino)carbonyl]-3,3-difluoropropyl}-L-leucinamide (484649-01-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/jm025594q

Reference yield:

methyl-(3-chloro-4-(2-aminoethyl))benzoate hydrochloride → N-(isobutoxycarbonyl)-L-valyl-N1-{(1S)-1-[({2-[2-chloro-4-(methoxycarbonyl)phenyl]ethyl}-amino)carbonyl]-3,3-difluoropropyl}-L-leucinamide (484649-01-6)

Guidance literature:

Multi-step reaction with 7 steps

1: EDCI; HOBt; DIPEA / CH₂Cl₂ / 20 °C

2: 98 percent / trifluoromethanesulfonic acid / CH₂Cl₂ / 0.08 h / 20 °C

3: 65 percent / 1-[3-(dimethylamino)propyl]-3-Etcarbodiimide hydrochloride; 1-hydroxybenzotriazole / CH₂Cl₂; dimethylformamide / 20 °C

4: 100 percent / HCl / methanol / 7 h / 20 °C

5: N,N-diisopropylethylamine; 1-[3-(dimethylamino)propyl]-3-Etcarbodiimide hydrochloride; 1-hydroxybenzotriazole / dimethylformamide; CH₂Cl₂

6: piperidine / dimethylformamide / 0.5 h / 20 °C

7: 90 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 0.5 h / 20 °C

With piperidine; hydrogenchloride; trifluorormethanesulfonic acid; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm025594q

Reference yield:

N1-{(1S)-1-[({2-[2-chloro-4-(methoxycarbonyl)phenyl]ethyl}amino)-carbonyl]-3,3-difluoropropyl}-L-leucinamide chloride → N-(isobutoxycarbonyl)-L-valyl-N1-{(1S)-1-[({2-[2-chloro-4-(methoxycarbonyl)phenyl]ethyl}-amino)carbonyl]-3,3-difluoropropyl}-L-leucinamide (484649-01-6)

Guidance literature:

Multi-step reaction with 3 steps

1: N,N-diisopropylethylamine; 1-[3-(dimethylamino)propyl]-3-Etcarbodiimide hydrochloride; 1-hydroxybenzotriazole / dimethylformamide; CH₂Cl₂

2: piperidine / dimethylformamide / 0.5 h / 20 °C

3: 90 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 0.5 h / 20 °C

With piperidine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm025594q

upstream raw materials:

isobutyl chloroformate

N-tert-butoxycarbonyl-L-leucine

methyl 3-chloro-4-methyl-benzoate

methyl 4-Bromomethyl-3-chlorobenzoate

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