N²-[4-(N-2,4-dimethoxybenzyloxyamino)-2R-isobutyl-3S-aminosuccinyl]-L-tert-leucine-N¹-methylamide

Base Information

• Chemical Name: N²-[4-(N-2,4-dimethoxybenzyloxyamino)-2R-isobutyl-3S-aminosuccinyl]-L-tert-leucine-N¹-methylamide
• CAS No.: 233749-19-4
• Molecular Formula: C₂₄H₄₀N₄O₆
• Molecular Weight: 480.605

Synonyms:N²-[4-(N-2,4-dimethoxybenzyloxyamino)-2R-isobutyl-3S-aminosuccinyl]-L-tert-leucine-N¹-methylamide

Chemical Property of N²-[4-(N-2,4-dimethoxybenzyloxyamino)-2R-isobutyl-3S-aminosuccinyl]-L-tert-leucine-N¹-methylamide

Chemical Property:

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Technology Process of N²-[4-(N-2,4-dimethoxybenzyloxyamino)-2R-isobutyl-3S-aminosuccinyl]-L-tert-leucine-N¹-methylamide

There total 5 articles about N²-[4-(N-2,4-dimethoxybenzyloxyamino)-2R-isobutyl-3S-aminosuccinyl]-L-tert-leucine-N¹-methylamide 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: 92.0%

[(1S,2R)-1-(2,4-Dimethoxy-benzyloxycarbamoyl)-2-((S)-2,2-dimethyl-1-methylcarbamoyl-propylcarbamoyl)-4-methyl-pentyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (233749-49-0) → N2-[4-(N-2,4-dimethoxybenzyloxyamino)-2R-isobutyl-3S-aminosuccinyl]-L-tert-leucine-N1-methylamide (233749-19-4)

Guidance literature:

With piperidine; In N,N-dimethyl-formamide; for 1h;

DOI:10.1016/S0040-4020(99)00347-6

Reference yield:

(S)-2-amino-N,3,3-trimethylbutanamide (89226-12-0) → N2-[4-(N-2,4-dimethoxybenzyloxyamino)-2R-isobutyl-3S-aminosuccinyl]-L-tert-leucine-N1-methylamide (233749-19-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 4.0 g / EDCI / CH₂Cl₂ / 3 h

2: 99 percent / trifluoroacetic acid / CH₂Cl₂ / 18 h / 0 °C

3: 75 percent / EDCI / dimethylformamide / 18 h / 20 °C

4: 92 percent / piperidine / dimethylformamide / 1 h

With piperidine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Hydrolysis / 3: Condensation / 4: Hydrolysis;

DOI:10.1016/S0040-4020(99)00347-6

Reference yield:

3(R/S)-(9-fluorenylmethoxycarbonylamino)-2R-isobutylbutan-1,4-dioic acid 4-tert-butyl ester (204126-52-3) → N2-[4-(N-2,4-dimethoxybenzyloxyamino)-2R-isobutyl-3S-aminosuccinyl]-L-tert-leucine-N1-methylamide (233749-19-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 4.0 g / EDCI / CH₂Cl₂ / 3 h

2: 99 percent / trifluoroacetic acid / CH₂Cl₂ / 18 h / 0 °C

3: 75 percent / EDCI / dimethylformamide / 18 h / 20 °C

4: 92 percent / piperidine / dimethylformamide / 1 h

With piperidine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Hydrolysis / 3: Condensation / 4: Hydrolysis;

DOI:10.1016/S0040-4020(99)00347-6

upstream raw materials:

[(1S,2R)-1-(2,4-Dimethoxy-benzyloxycarbamoyl)-2-((S)-2,2-dimethyl-1-methylcarbamoyl-propylcarbamoyl)-4-methyl-pentyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

(S)-2-amino-N,3,3-trimethylbutanamide

3(R/S)-(9-fluorenylmethoxycarbonylamino)-2R-isobutylbutan-1,4-dioic acid 4-tert-butyl ester

N²-[2R-isobutyl-3S-(9-fluorenylmethoxycarbonylamino)-4-hydroxysuccinyl]-L-tert-leucine-N¹-methylamide

Downstream raw materials:

(R)-2-[(S)-1-(2,4-Dimethoxy-benzyloxy)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-5-oxo-imidazolidin-4-yl]-4-methyl-pentanoic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-amide

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