3(S)-bromo-4(R)-<(2,5-dihydroxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

Base Information

• Chemical Name: 3(S)-bromo-4(R)-<(2,5-dihydroxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one
• CAS No.: 99765-22-7
• Molecular Formula: C₁₅H₁₆BrNO₇S
• Molecular Weight: 434.265
• Mol file: 99765-22-7.mol

Synonyms:3(S)-bromo-4(R)-<(2,5-dihydroxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

Chemical Property of 3(S)-bromo-4(R)-<(2,5-dihydroxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3(S)-bromo-4(R)-<(2,5-dihydroxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

There total 4 articles about 3(S)-bromo-4(R)-<(2,5-dihydroxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one 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:

6α-Bromopenicillanic acid 1,1-dioxide methyl ester (98114-06-8) → 3(S)-bromo-4(R)-<(2,5-dihydroxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one (99765-22-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) DBU, 2.) CF₃COOH / tetrahydrofuran / 1.) 5 deg C, 1 h, 2.) 5 deg C, 5 min

2: tetrahydrofuran / Ambient temperature

With 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1021/jo00353a025

Reference yield:

6α-bromopenicillanic acid methyl ester (34800-34-5) → 3(S)-bromo-4(R)-<(2,5-dihydroxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one (99765-22-7)

Guidance literature:

Multi-step reaction with 3 steps

1: m-chloroperbenzoic acid / CH₂Cl₂ / Ambient temperature

2: 1.) DBU, 2.) CF₃COOH / tetrahydrofuran / 1.) 5 deg C, 1 h, 2.) 5 deg C, 5 min

3: tetrahydrofuran / Ambient temperature

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00353a025

Reference yield:

2-((3S,4R)-3-Bromo-2-oxo-4-sulfino-azetidin-1-yl)-3-methyl-but-2-enoic acid methyl ester + p-benzoquinone (106-51-4) → 3(S)-bromo-4(R)-<(2,5-dihydroxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one (99765-22-7)

Guidance literature:

In tetrahydrofuran; Yield given; Ambient temperature;

DOI:10.1021/jo00353a025

upstream raw materials:

6α-Bromopenicillanic acid 1,1-dioxide methyl ester

p-benzoquinone

6α-bromopenicillanic acid methyl ester

Downstream raw materials:

3(S)-<1(R)-hydroxyethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

3(S)-<1(S)-hydroxyethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

3(S)-<1(R)-<<(phenoxymethyl)carbonyl>oxy>ethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one

3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<(2,5-dimethoxyphenyl)sulfonyl>-1-<1-(methoxycarbonyl)-2-methyl-1-propen-1-yl>azetidin-2-one