2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester

Base Information

• Chemical Name: 2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester
• CAS No.: 1309451-06-6
• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.337
• Mol file: 1309451-06-6.mol

Synonyms:2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester

Chemical Property of 2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester

Chemical Property:

Purity/Quality:

98.5% ^*data from raw suppliers

Benzyl-Peg2-Ch2co2tbu ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Benzyl-PEG2-CH2CO2tBu is a PEG linker containing a benzyl group and a t-butyl protected carbonyl. Both the benzyl and t-Butyl group can be removed under acidic conditions. The carboxylic acid can be reacted with primary amines in the presence of activators such as EDC and DCC to form stable amide bonds. The hydrophilic PEG linkers increase the water solubility of the compound in aqueous media.

Technology Process of 2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester

There total 2 articles about 2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl 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: 86.0%

bromoacetic acid tert-butyl ester (5292-43-3) + 2-Benzyloxyethanol (622-08-2,1201808-31-2) → 2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester (1309451-06-6)

Guidance literature:

With tetrabutyl-ammonium chloride; sodium hydroxide; In dichloromethane; at 20 ℃; for 4h;

Reference yield:

benzyl bromide (100-39-0) → 2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester (1309451-06-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / 16 h / 20 °C / Inert atmosphere

1.2: 70 °C

2.1: potassium tert-butylate / tert-butyl alcohol / 0.5 h / 20 °C / Inert atmosphere

2.2: 16 h / 20 °C / Inert atmosphere

With potassium tert-butylate; sodium hydride; In tert-butyl alcohol;

DOI:10.1021/ic400227k

Reference yield: 95.0%

2-(2-(benzyloxy)ethoxy)acetic acid tert-butyl ester (1309451-06-6) → <2-(benzyloxy)ethoxy>acetic acid (93206-09-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

upstream raw materials:

bromoacetic acid tert-butyl ester

2-Benzyloxyethanol

benzyl bromide

Downstream raw materials:

<2-(benzyloxy)ethoxy>acetic acid

(2-hydroxyethoxy)acetic acid tert-butyl ester

tert-butyl 2-(2-[[(4-methylbenzene)sulfonyl]oxy]ethoxy)acetate

2-azidoethoxyacetic acid tert-butyl ester

Refernces

• 1、 -. "Protein degradation targeting chimera for degrading androgen receptor". Paragraph 0218-0220; 0224-0226. . Retrieved 2021/07/24.
• 2、 -. "Compound for targeted ubiquitination degradation of ERRalpha protein and pharmaceutical composition and application thereof". Paragraph 0299-0302. . Retrieved 2020/06/20.