(-)-tert-butyl (2R)-3-(3-amino-4-chloro-2-methylphenyl)-2-methylpropanoate

Base Information

• Chemical Name: (-)-tert-butyl (2R)-3-(3-amino-4-chloro-2-methylphenyl)-2-methylpropanoate
• CAS No.: 1297551-22-4
• Molecular Formula: C₁₅H₂₂ClNO₂
• Molecular Weight: 283.798
• Mol file: 1297551-22-4.mol

Synonyms:(-)-tert-butyl (2R)-3-(3-amino-4-chloro-2-methylphenyl)-2-methylpropanoate

Chemical Property of (-)-tert-butyl (2R)-3-(3-amino-4-chloro-2-methylphenyl)-2-methylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-tert-butyl (2R)-3-(3-amino-4-chloro-2-methylphenyl)-2-methylpropanoate

There total 4 articles about (-)-tert-butyl (2R)-3-(3-amino-4-chloro-2-methylphenyl)-2-methylpropanoate 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:

(+/-)-tert-butyl 3-(3-amino-4-chloro-2-methylphenyl)-2-methylpropanoate (1297551-19-9) → (+)-tert-butyl (2S)-3-(3-amino-4-chloro-2-methylphenyl)-2-methylpropanoate (1297551-23-5) + (-)-tert-butyl (2R)-3-(3-amino-4-chloro-2-methylphenyl)-2-methylpropanoate (1297551-22-4)

Guidance literature:

With Daicel Chiralpak OJ-H; In 2-Methylpentane; isopropyl alcohol; at 22 ℃; Resolution of racemate;

Reference yield:

3-bromo-6-chloro-2-methylaniline (1007226-77-8) → (+)-tert-butyl (2S)-3-(3-amino-4-chloro-2-methylphenyl)-2-methylpropanoate (1297551-23-5) + (-)-tert-butyl (2R)-3-(3-amino-4-chloro-2-methylphenyl)-2-methylpropanoate (1297551-22-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 2 h / 150 °C / Inert atmosphere

2.1: iodine; magnesium / methanol / 20 °C

2.2: Cooling with ice

2.3: pH 10

3.1: Daicel Chiralpak OJ-H / isopropyl alcohol; 2-Methylpentane / 22 °C / Resolution of racemate

With iodine; magnesium; triethylamine; palladium diacetate; tris-(o-tolyl)phosphine; In methanol; 2-Methylpentane; N,N-dimethyl-formamide; isopropyl alcohol;

Reference yield:

3-bromo-2-methylaniline (55289-36-6) → (+)-tert-butyl (2S)-3-(3-amino-4-chloro-2-methylphenyl)-2-methylpropanoate (1297551-23-5) + (-)-tert-butyl (2R)-3-(3-amino-4-chloro-2-methylphenyl)-2-methylpropanoate (1297551-22-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-chloro-succinimide / acetonitrile / 7 h / 60 °C

2.1: triethylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 2 h / 150 °C / Inert atmosphere

3.1: iodine; magnesium / methanol / 20 °C

3.2: Cooling with ice

3.3: pH 10

4.1: Daicel Chiralpak OJ-H / isopropyl alcohol; 2-Methylpentane / 22 °C / Resolution of racemate

With N-chloro-succinimide; iodine; magnesium; triethylamine; palladium diacetate; tris-(o-tolyl)phosphine; In methanol; 2-Methylpentane; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;

upstream raw materials:

3-bromo-2-methylaniline

3-bromo-6-chloro-2-methylaniline

tert-butyl 2-(3-amino-4-chloro-2-methylbenzyl)acrylate

(+/-)-tert-butyl 3-(3-amino-4-chloro-2-methylphenyl)-2-methylpropanoate

Downstream raw materials:

(+)-tert-butyl (2R)-3-(4-chloro-3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methyl-butanoyl]amino}-2-methylphenyl)-2-methylpropanoate