(3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(bromomethyl)-2-azetidinone

Base Information

• Chemical Name: (3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(bromomethyl)-2-azetidinone
• CAS No.: 160238-00-6
• Molecular Formula: C₁₈H₁₈BrNO₃
• Molecular Weight: 376.25

Synonyms:(3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(bromomethyl)-2-azetidinone

Chemical Property of (3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(bromomethyl)-2-azetidinone

Chemical Property:

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Technology Process of (3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(bromomethyl)-2-azetidinone

There total 2 articles about (3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(bromomethyl)-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: 83.0%

(3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(hydroxymethyl)-2-azetidinone (160237-99-0) → (3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(bromomethyl)-2-azetidinone (160238-00-6)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; at 25 ℃; for 2h;

DOI:10.1021/jm00043a005

Reference yield:

n-propylmagnesium bromide (927-77-5) + Trifluoro-methanesulfonic acid (2S,3R)-3-benzyloxy-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-ylmethyl ester → (3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(hydroxymethyl)-2-azetidinone (160237-99-0) + (3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(bromomethyl)-2-azetidinone (160238-00-6) + (3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-butyl-2-azetidinone

Guidance literature:

With copper(I) bromide; Yield given. Multistep reaction; 1.) THF, 0 deg C, 10 min, 2.) THF, 3 h;

DOI:10.1021/jm00043a005

Reference yield: 78.0%

(3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(bromomethyl)-2-azetidinone (160238-00-6) + methyl iodide (74-88-4) → (3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(methoxymethyl)-2-azetidinone

Guidance literature:

With silver(l) oxide; Heating;

DOI:10.1021/jm00043a005

upstream raw materials:

n-propylmagnesium bromide

(3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(hydroxymethyl)-2-azetidinone

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