(+/-)-<3α(S^*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-t-butoxycarbonyl-2-azetidinone-4-carboxylic acid

Base Information

• Chemical Name: (+/-)-<3α(S^*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-t-butoxycarbonyl-2-azetidinone-4-carboxylic acid
• CAS No.: 87325-91-5
• Molecular Formula: C₂₀H₂₇NO₈
• Molecular Weight: 409.436

Synonyms:(+/-)-<3α(S^*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-t-butoxycarbonyl-2-azetidinone-4-carboxylic acid

Chemical Property of (+/-)-<3α(S^*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-t-butoxycarbonyl-2-azetidinone-4-carboxylic acid

Chemical Property:

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Technology Process of (+/-)-<3α(S^*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-t-butoxycarbonyl-2-azetidinone-4-carboxylic acid

There total 2 articles about (+/-)-<3α(S^*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-t-butoxycarbonyl-2-azetidinone-4-carboxylic acid 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:

(+/-)-<3α(S*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-acetoxyethyl)-4-ethoxycarbonyl-4-t-butoxycarbonyl-2-azetidinone (87325-90-4) → (+/-)-<3α(S*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-t-butoxycarbonyl-2-azetidinone-4-carboxylic acid (87325-91-5)

Guidance literature:

With sodium hydroxide; In pyridine; at 0 ℃;

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

Reference yield:

(+/-)-<3S-<3α(S*),4α>>-1-(2,4-dimethoxybenzyl)-3-(1-acetoxyethyl)-4-ethoxycarbonyl-2-azetidinone-4-carboxylic acid (81902-52-5,87479-86-5) → (+/-)-<3α(S*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-t-butoxycarbonyl-2-azetidinone-4-carboxylic acid (87325-91-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) oxalyl chloride, 2.) pyridine / 1.) reflux, 30 min, THF 2.) reflux, 4 h, THF

2: 36 mg / 0.1N NaOH / pyridine / 0 °C

With pyridine; sodium hydroxide; oxalyl dichloride; In pyridine;

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

Reference yield: 84.0%

(+/-)-<3α(S*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-t-butoxycarbonyl-2-azetidinone-4-carboxylic acid (87325-91-5) → (+/-)-<1α,4α,5α>-t-butyl-7-(2,4-dimethoxybenzyl)-2,6-dioxo-4-methyl-3-oxa-7-azabicyclo<3.2.0>heptane-1-carboxylate (81902-66-1,85550-27-2)

Guidance literature:

With acetic anhydride; In pyridine; at 15 ℃; for 20h;

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

upstream raw materials:

(+/-)-<3α(S^*),4β>-1-(2,4-dimethoxybenzyl)-3-(1-acetoxyethyl)-4-ethoxycarbonyl-4-t-butoxycarbonyl-2-azetidinone

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

Downstream raw materials:

(+/-)-<1α,4α,5α>-t-butyl-7-(2,4-dimethoxybenzyl)-2,6-dioxo-4-methyl-3-oxa-7-azabicyclo<3.2.0>heptane-1-carboxylate

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