2-(RS)-benzyl-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester

Base Information

• Chemical Name: 2-(RS)-benzyl-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester
• CAS No.: 253593-05-4
• Molecular Formula: C₁₆H₂₂O₄
• Molecular Weight: 278.348
• Mol file: 253593-05-4.mol

Synonyms:2-(RS)-benzyl-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester

Chemical Property of 2-(RS)-benzyl-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(RS)-benzyl-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester

There total 3 articles about 2-(RS)-benzyl-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester 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: 46.0%

2-benzyl-2-methoxycarbonyl-succinic acid 4-tert-butyl ester 1-methyl ester → 2-(RS)-benzyl-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester (253593-05-4)

Guidance literature:

With lithium bromide; In N,N-dimethyl-formamide; at 135 ℃; for 8h;

DOI:10.1016/S0957-4166(99)00330-4

Reference yield:

2-benzyl-malonic acid dimethyl ester (49769-78-0) → 2-(RS)-benzyl-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester (253593-05-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 0 °C

1.2: tetrahydrofuran / 3.5 h / 20 °C

2.1: 46 percent / aq. lithium bromide / dimethylformamide / 8 h / 135 °C

With sodium hexamethyldisilazane; lithium bromide; In tetrahydrofuran; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Alkylation / 2.1: demethoxycarbonylation;

DOI:10.1016/S0957-4166(99)00330-4

Reference yield:

benzyl bromide (100-39-0) → 2-(RS)-benzyl-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester (253593-05-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaOMe / methanol

1.2: methanol / 14 h / 20 °C

2.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 0 °C

2.2: tetrahydrofuran / 3.5 h / 20 °C

3.1: 46 percent / aq. lithium bromide / dimethylformamide / 8 h / 135 °C

With sodium methylate; sodium hexamethyldisilazane; lithium bromide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Alkylation / 2.1: Metallation / 2.2: Alkylation / 3.1: demethoxycarbonylation;

DOI:10.1016/S0957-4166(99)00330-4

upstream raw materials:

2-benzyl-malonic acid dimethyl ester

benzyl bromide

Downstream raw materials:

(2R)-3-tert-Butyloxycarbonyl-2-phenylmethylpropionic Acid