METHYL-(2E)-2-ACETYLAMINO-3-BROMO-2-BUTENOATE

Base Information

• Chemical Name: METHYL-(2E)-2-ACETYLAMINO-3-BROMO-2-BUTENOATE
• CAS No.: 188656-15-7
• Molecular Formula: C7H10 Br N O3
• Molecular Weight: 236.06
• Mol file: 188656-15-7.mol

Synonyms:2-Butenoicacid, 2-(acetylamino)-3-bromo-, methyl ester, (E)-

Chemical Property of METHYL-(2E)-2-ACETYLAMINO-3-BROMO-2-BUTENOATE

Chemical Property:

• Vapor Pressure: 3.71E-05mmHg at 25°C
• Refractive Index: 1.504
• Boiling Point: 352.9°Cat760mmHg
• Flash Point: 167.3°C
• PSA: 55.40000
• Density: 1.476g/cm³
• LogP: 1.31280

Purity/Quality:

98% ^*data from raw suppliers

METHYL-(2E)-2-ACETYLAMINO-3-BROMO-2-BUTENOATE 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of METHYL-(2E)-2-ACETYLAMINO-3-BROMO-2-BUTENOATE

There total 5 articles about METHYL-(2E)-2-ACETYLAMINO-3-BROMO-2-BUTENOATE 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: 84.0%

(Z)-methyl 2-acetamido-3-methoxyacrylate (57294-56-1,60027-53-4,60027-59-0) → (E)-methyl-2-acetamido-3-bromobut-2-enoate (188656-15-7) + (Z)-2-Acetylamino-3-bromo-but-2-enoic acid methyl ester (188656-16-8)

Guidance literature:

With N-Bromosuccinimide; triethylamine; Yields of byproduct given;

DOI:10.1016/S0040-4039(98)00604-2

Reference yield: 78.0%

(Z)-methyl 2-acetamido-3-methoxyacrylate (57294-56-1,60027-53-4,60027-59-0) → (E)-methyl-2-acetamido-3-bromobut-2-enoate (188656-15-7)

Guidance literature:

(Z)-methyl 2-acetamido-3-methoxyacrylate; With N-Bromosuccinimide; In dichloromethane; at 20 ℃;

With lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; at -78 ℃;

DOI:10.1021/jm101013m

Reference yield:

L-threonine methyl ester (3373-59-9) → (E)-methyl-2-acetamido-3-bromobut-2-enoate (188656-15-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaOAc

2.1: Et₃N / methanol

3.1: NBS / CH₂Cl₂

3.2: Et₃N / CH₂Cl₂

With N-Bromosuccinimide; sodium acetate; triethylamine; In methanol; dichloromethane;

DOI:10.1021/ja049499d

upstream raw materials:

(Z)-methyl 2-acetamido-3-methoxyacrylate

L-threonine methyl ester

methyl (2S,3R)-2-(acetylamino)-3-hydroxybutanoate

methyl 2-acetylamino-2-(dimethoxyphosphinyl)acetate

Downstream raw materials:

methyl (E)-2-(N-acetylamino)-3-phenyl-2-butenoate

Refernces

• 1、 Zhou, Changyou,Garcia-Calvo, Margareta,Pinto, Shirly,Lombardo, Matthew,Feng, Zhe,Bender, Kate,Pryor, Kellyann D.,Bhatt, Urmi R.,Chabin, Renee M.,Geissler, Wayne M.,Shen, Zhu,Tong, Xinchun,Zhang, Zhoupeng,Wong, Kenny K.,Roy, Ranabir Sinha,Chapman, Kevin T.,Yang, Lihu,Xiong, Yusheng. "Design and synthesis of prolylcarboxypeptidase (PrCP) inhibitors to validate PrCP as a potential target for obesity". experimental part. p. 7251 - 7263. Retrieved 2010/12/25.
• 2、 Hoerrner, R. Scott,Askin, David,Volante, R. P.,Reider, Paul J.. "A Highly Enantioselective Asymmetric Hydrogenation Route to β-(2R,3S)-Methyltryptophan". . p. 3455 - 3458. Retrieved 2007/10/03.