(+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propynyl)-2-azetidinone

Base Information

• Chemical Name: (+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propynyl)-2-azetidinone
• CAS No.: 276244-06-5
• Molecular Formula: C₁₈H₂₁NO₅
• Molecular Weight: 331.368
• Mol file: 276244-06-5.mol

Synonyms:(+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propynyl)-2-azetidinone

Chemical Property of (+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propynyl)-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propynyl)-2-azetidinone

There total 5 articles about (+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propynyl)-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: 70.0%

propargyl bromide (106-96-7) + (S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)azetidine-2,3-dione (153463-32-2) → (+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propynyl)-2-azetidinone (276244-06-5)

Guidance literature:

With ammonium chloride; zinc; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/jo015704l

Reference yield:

(3R,4S)-cis-1-(p-anisyl)-3-hydroxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (115828-87-0) → (+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propynyl)-2-azetidinone (276244-06-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

2: 70 percent / zinc; aq. NH₄Cl / tetrahydrofuran / 0 °C

With oxalyl dichloride; ammonium chloride; dimethyl sulfoxide; triethylamine; zinc; In tetrahydrofuran; dichloromethane; 1: Swern oxidation;

DOI:10.1021/jo015704l

Reference yield:

[1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine (141781-24-0) → (+)-(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propynyl)-2-azetidinone (276244-06-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / Et₃N / CH₂Cl₂ / 16 h / 20 °C

2: 86 percent / sodium methoxide / methanol / 0.33 h / 0 °C

3: 77 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

4: 70 percent / zinc; aq. NH₄Cl / tetrahydrofuran / 0 °C

With oxalyl dichloride; sodium methylate; ammonium chloride; dimethyl sulfoxide; triethylamine; zinc; In tetrahydrofuran; methanol; dichloromethane; 1: Staudinger reaction / 3: Swern oxidation;

DOI:10.1021/jo015704l

upstream raw materials:

propargyl bromide

(S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)azetidine-2,3-dione

(3R,4S)-cis-1-(p-anisyl)-3-hydroxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

[1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine

Downstream raw materials:

C₃₃H₃₆N₂O₉