(3S)-N-(benzyloxy)-2-bromo-N-((3S)-1-(methoxyamino)-3-methyl-1-oxopentan-2-yl)-3-methylpentanamide

Base Information

• Chemical Name: (3S)-N-(benzyloxy)-2-bromo-N-((3S)-1-(methoxyamino)-3-methyl-1-oxopentan-2-yl)-3-methylpentanamide
• CAS No.: 1264728-31-5
• Molecular Formula: C₂₀H₃₁BrN₂O₄
• Molecular Weight: 443.381

Synonyms:(3S)-N-(benzyloxy)-2-bromo-N-((3S)-1-(methoxyamino)-3-methyl-1-oxopentan-2-yl)-3-methylpentanamide

Chemical Property of (3S)-N-(benzyloxy)-2-bromo-N-((3S)-1-(methoxyamino)-3-methyl-1-oxopentan-2-yl)-3-methylpentanamide

Chemical Property:

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Technology Process of (3S)-N-(benzyloxy)-2-bromo-N-((3S)-1-(methoxyamino)-3-methyl-1-oxopentan-2-yl)-3-methylpentanamide

There total 5 articles about (3S)-N-(benzyloxy)-2-bromo-N-((3S)-1-(methoxyamino)-3-methyl-1-oxopentan-2-yl)-3-methylpentanamide 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: 65.0%

(3S)-2-((benzyloxy)amino)-N-methoxy-3-methylpentanamide (1264728-30-4) + (3S)-2-bromo-3-methylpentanoyl chloride → (3S)-N-(benzyloxy)-2-bromo-N-((3S)-1-(methoxyamino)-3-methyl-1-oxopentan-2-yl)-3-methylpentanamide (1264728-31-5)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 3.11667h; Inert atmosphere;

DOI:10.1021/jo102228j

Reference yield:

L-isoleucine (73-32-5,959215-79-3,18875-42-8) → (3S)-N-(benzyloxy)-2-bromo-N-((3S)-1-(methoxyamino)-3-methyl-1-oxopentan-2-yl)-3-methylpentanamide (1264728-31-5)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogen bromide; sodium nitrite / water / 4 h / 0 °C / Inert atmosphere

2: thionyl chloride / chloroform / Inert atmosphere; Reflux

3: triethylamine / dichloromethane / 3.12 h / 20 °C / Inert atmosphere

With thionyl chloride; hydrogen bromide; triethylamine; sodium nitrite; In dichloromethane; chloroform; water;

DOI:10.1021/jo102228j

Reference yield:

(3S)-2-bromo-N-methoxy-3-methylpentanamide (1264728-29-1) → (3S)-N-(benzyloxy)-2-bromo-N-((3S)-1-(methoxyamino)-3-methyl-1-oxopentan-2-yl)-3-methylpentanamide (1264728-31-5)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / tetrahydrofuran / 1.5 h / 85 °C / Inert atmosphere

2: triethylamine / dichloromethane / 3.12 h / 20 °C / Inert atmosphere

With potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo102228j

upstream raw materials:

(3S)-2-((benzyloxy)amino)-N-methoxy-3-methylpentanamide

(3S)-2-bromo-N-methoxy-3-methylpentanamide

L-isoleucine

N-benzyloxyamine

Downstream raw materials:

1-(benzyloxy)-3,6-di((S)-sec-butyl)-4-methoxypiperazine-2,5-dione

4-(benzyloxy)-2,5-di((S)-sec-butyl)-6-(methoxyimino)morpholin-3-one

3,6-di((S)-sec-butyl)-3-hydroxy-1-methoxy-4-phenoxypiperazine-2,5-dione

3,6-di((S)-sec-butyl)-3-hydroxy-1-methoxy-4-(2-methoxyphenoxy)piperazine-2,5-dione

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