<3S(R)>-1-(2,4-dimethoxybenzyl)-3-(1-acetoxyethyl)-4,4-bis(ethoxycarbonyl)-2-azetidinone

Base Information

• Chemical Name: <3S(R)>-1-(2,4-dimethoxybenzyl)-3-(1-acetoxyethyl)-4,4-bis(ethoxycarbonyl)-2-azetidinone
• CAS No.: 81902-51-4
• Molecular Formula: C₂₂H₂₉NO₉
• Molecular Weight: 451.474
• Mol file: 81902-51-4.mol

Synonyms:<3S(R)>-1-(2,4-dimethoxybenzyl)-3-(1-acetoxyethyl)-4,4-bis(ethoxycarbonyl)-2-azetidinone

Chemical Property of <3S(R)>-1-(2,4-dimethoxybenzyl)-3-(1-acetoxyethyl)-4,4-bis(ethoxycarbonyl)-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3S(R)>-1-(2,4-dimethoxybenzyl)-3-(1-acetoxyethyl)-4,4-bis(ethoxycarbonyl)-2-azetidinone

There total 5 articles about <3S(R)>-1-(2,4-dimethoxybenzyl)-3-(1-acetoxyethyl)-4,4-bis(ethoxycarbonyl)-2-azetidinone 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: 96.0%

(2R,3R)-N-2,4-dimethoxybenzyl-N-bis(ethoxycarbonyl)methyl-2-bromo-3-acetoxybutylamide (81902-50-3) → <3S(R)>-1-(2,4-dimethoxybenzyl)-3-(1-acetoxyethyl)-4,4-bis(ethoxycarbonyl)-2-azetidinone (81902-51-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; at 20 ℃; for 15h;

DOI:10.1016/S0040-4039(01)92460-8

Reference yield:

diethyl N-(2,4-dimethoxybenzyl)-amino-malonate (81902-49-0) → <3S(R)>-1-(2,4-dimethoxybenzyl)-3-(1-acetoxyethyl)-4,4-bis(ethoxycarbonyl)-2-azetidinone (81902-51-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / triethylamine / tetrahydrofuran / 15 h / 20 °C

2: 95.9 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / Ambient temperature

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; benzene;

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

Reference yield:

(2R,3R)-2-bromo-3-acetoxy-butyryl chloride (81968-19-6) → <3S(R)>-1-(2,4-dimethoxybenzyl)-3-(1-acetoxyethyl)-4,4-bis(ethoxycarbonyl)-2-azetidinone (81902-51-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / triethylamine / tetrahydrofuran / 15 h / 20 °C

2: 95.9 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / Ambient temperature

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; benzene;

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

upstream raw materials:

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

diethyl aminomalonate hydrochloride

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

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

Downstream raw materials:

<3S-<3α(S^*),4α>>-1-(2,4-dimethoxybenzyl)-3-(1-acetoxyethyl)-4-ethoxycarbonyl-2-azetidinone-4-carboxylic acid

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

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

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