Benzenebutanoic acid, 4-[(1,1-dimethylethoxy)carbonyl]--alpha--methyl-, (-alpha-S)- (9CI)

Base Information

• Chemical Name: Benzenebutanoic acid, 4-[(1,1-dimethylethoxy)carbonyl]--alpha--methyl-, (-alpha-S)- (9CI)
• CAS No.: 738627-74-2
• Molecular Formula: C16H22 O4
• Molecular Weight: 278.34
• Mol file: 738627-74-2.mol

Synonyms:Benzenebutanoic acid, 4-[(1,1-dimethylethoxy)carbonyl]--alpha--methyl-, (-alpha-S)- (9CI)

Chemical Property of Benzenebutanoic acid, 4-[(1,1-dimethylethoxy)carbonyl]--alpha--methyl-, (-alpha-S)- (9CI)

Chemical Property:

• PSA: 63.60000
• LogP: 3.29520

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzenebutanoic acid, 4-[(1,1-dimethylethoxy)carbonyl]--alpha--methyl-, (-alpha-S)- (9CI)

There total 4 articles about Benzenebutanoic acid, 4-[(1,1-dimethylethoxy)carbonyl]--alpha--methyl-, (-alpha-S)- (9CI) 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: 79.0%

4-[(3R)-4-(10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-methyl-4-oxo-butyl]-benzoic acid tert-butyl ester → 4-[(3S)-3-carboxy-3-methyl-propyl]-benzoic acid tert-butyl ester (738627-74-2)

Guidance literature:

With lithium hydroxide; tetrabutylammomium bromide; lithium bromide; In acetonitrile; at 20 ℃;

DOI:10.1016/j.bmc.2004.03.006

Reference yield:

tert-butyl-4-bromobenzoate (59247-47-1) → 4-[(3S)-3-carboxy-3-methyl-propyl]-benzoic acid tert-butyl ester (738627-74-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 76 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 48 h / 20 °C

2.1: 63 percent / trimethylaluminium / toluene; hexane / 50 °C

3.1: 1,1,1,3,3,3-hexamethyldisilazane; n-butyllithium / tetrahydrofuran; hexane / -78 °C

3.2: 48 percent / tetrahydrofuran; hexane / 2 h / -78 °C

4.1: 79 percent / lithium hydroxide; lithium bromide; tetrabutylammonium bromide / acetonitrile / 20 °C

With lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; tetrabutylammomium bromide; trimethylaluminum; 1,1,1,3,3,3-hexamethyl-disilazane; lithium bromide; In tetrahydrofuran; hexane; toluene; acetonitrile;

DOI:10.1016/j.bmc.2004.03.006

Reference yield:

4-(3-ethoxycarbonyl-propyl)-benzoic acid tert-butyl ester (738627-66-2) → 4-[(3S)-3-carboxy-3-methyl-propyl]-benzoic acid tert-butyl ester (738627-74-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 63 percent / trimethylaluminium / toluene; hexane / 50 °C

2.1: 1,1,1,3,3,3-hexamethyldisilazane; n-butyllithium / tetrahydrofuran; hexane / -78 °C

2.2: 48 percent / tetrahydrofuran; hexane / 2 h / -78 °C

3.1: 79 percent / lithium hydroxide; lithium bromide; tetrabutylammonium bromide / acetonitrile / 20 °C

With lithium hydroxide; n-butyllithium; tetrabutylammomium bromide; trimethylaluminum; 1,1,1,3,3,3-hexamethyl-disilazane; lithium bromide; In tetrahydrofuran; hexane; toluene; acetonitrile;

DOI:10.1016/j.bmc.2004.03.006

upstream raw materials:

tert-butyl-4-bromobenzoate

4-(3-ethoxycarbonyl-propyl)-benzoic acid tert-butyl ester

Downstream raw materials:

4-[(3R)-3-[(1S)-1-((1S)-2-benzo[b]thiophen-3-yl-1-benzylcarbamoyl-ethylcarbamoyl)-2-biphenyl-4-yl-ethylcarbamoyl]-3-methyl-propyl]-benzoic acid tert-butyl ester

Refernces