(2R,3R)-N-2,4-dimethoxybenzyl-N-bis(ethoxycarbonyl)methyl-2-bromo-3-acetoxybutylamide

Base Information

• Chemical Name: (2R,3R)-N-2,4-dimethoxybenzyl-N-bis(ethoxycarbonyl)methyl-2-bromo-3-acetoxybutylamide
• CAS No.: 81902-50-3
• Molecular Formula: C₂₂H₃₀BrNO₉
• Molecular Weight: 532.385

Synonyms:(2R,3R)-N-2,4-dimethoxybenzyl-N-bis(ethoxycarbonyl)methyl-2-bromo-3-acetoxybutylamide

Chemical Property of (2R,3R)-N-2,4-dimethoxybenzyl-N-bis(ethoxycarbonyl)methyl-2-bromo-3-acetoxybutylamide

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Technology Process of (2R,3R)-N-2,4-dimethoxybenzyl-N-bis(ethoxycarbonyl)methyl-2-bromo-3-acetoxybutylamide

There total 3 articles about (2R,3R)-N-2,4-dimethoxybenzyl-N-bis(ethoxycarbonyl)methyl-2-bromo-3-acetoxybutylamide 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: 97.0%

diethyl N-(2,4-dimethoxybenzyl)-amino-malonate (81902-49-0) + (2R,3R)-2-bromo-3-acetoxy-butyryl chloride (81968-19-6) → (2R,3R)-N-2,4-dimethoxybenzyl-N-bis(ethoxycarbonyl)methyl-2-bromo-3-acetoxybutylamide (81902-50-3)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 15h;

DOI:10.1016/S0040-4020(01)91966-0

Reference yield:

diethyl aminomalonate hydrochloride (13433-00-6) → (2R,3R)-N-2,4-dimethoxybenzyl-N-bis(ethoxycarbonyl)methyl-2-bromo-3-acetoxybutylamide (81902-50-3)

Guidance literature:

Multi-step reaction with 2 steps

2: 97 percent / triethylamine / tetrahydrofuran / 15 h / 20 °C

With triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)91966-0

Reference yield:

2,4-Dimethoxybenzaldehyde (613-45-6) → (2R,3R)-N-2,4-dimethoxybenzyl-N-bis(ethoxycarbonyl)methyl-2-bromo-3-acetoxybutylamide (81902-50-3)

Guidance literature:

Multi-step reaction with 2 steps

2: 97 percent / triethylamine / tetrahydrofuran / 15 h / 20 °C

With triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)91966-0

upstream raw materials:

diethyl N-(2,4-dimethoxybenzyl)-amino-malonate

(2R,3R)-2-bromo-3-acetoxy-butyryl chloride

diethyl aminomalonate hydrochloride

2,4-Dimethoxybenzaldehyde

Downstream raw materials:

(3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(benzyloxycarbonyl)methyl>-2-azetidinone

<3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-diazoacetyl-2-azetidinone

[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(2,4-dimethoxy-benzyl)-4-oxo-azetidin-2-yl]-acetic acid methyl ester

<3S-<3α(S^*),4β>>-benzyl<1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-yl>acetate

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