(S)-2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoic acid

Base Information

• Chemical Name: (S)-2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoic acid
• CAS No.: 478183-60-7
• Molecular Formula: C12H21NO4
• Molecular Weight: 243.303
• Hs Code.: 2924299090
• Mol file: 478183-60-7.mol

Synonyms:(S)-2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoic acid

Chemical Property of (S)-2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoic acid

Chemical Property:

• PSA: 75.63000
• LogP: 2.54540
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

(S)-2-((tert-Butoxycarbonyl)amino)-3-cyclobutylpropanoicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoic acid

There total 7 articles about (S)-2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoic acid 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:

(S)-2-amino-3-cyclobutylpropanoic acid (1201593-65-8,174266-00-3) + di-tert-butyl dicarbonate (24424-99-5) → (2S)-2-[[(tert-butoxy)carbonyl]amino]-3-cyclobutylpropanoic acid (478183-60-7)

Guidance literature:

With sodium hydroxide; In water; acetone; at 20 ℃; for 12h; pH=8;

DOI:10.1021/acs.jmedchem.8b01201

Reference yield:

cyclobutanemethanol (4415-82-1) → (2S)-2-[[(tert-butoxy)carbonyl]amino]-3-cyclobutylpropanoic acid (478183-60-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C

2.1: sodium iodide / acetone / 12 h / 60 °C

3.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.5 h / 10 °C

3.2: 10 h / 20 °C

4.1: sodium hydroxide / water; ethanol / 8 h / Reflux

5.1: sodium hydroxide; L-acylase / water / 40 h / 37 °C / pH 7.5 / Enzymatic reaction

6.1: sodium hydroxide / water; acetone / 12 h / 20 °C / pH 8

With L-acylase; potassium tert-butylate; triethylamine; sodium iodide; sodium hydroxide; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/acs.jmedchem.8b01201

Reference yield:

cyclobutylmethyl methanesulfonate (63659-30-3) → (2S)-2-[[(tert-butoxy)carbonyl]amino]-3-cyclobutylpropanoic acid (478183-60-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium iodide / acetone / 12 h / 60 °C

2.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.5 h / 10 °C

2.2: 10 h / 20 °C

3.1: sodium hydroxide / water; ethanol / 8 h / Reflux

4.1: sodium hydroxide; L-acylase / water / 40 h / 37 °C / pH 7.5 / Enzymatic reaction

5.1: sodium hydroxide / water; acetone / 12 h / 20 °C / pH 8

With L-acylase; potassium tert-butylate; sodium iodide; sodium hydroxide; In ethanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/acs.jmedchem.8b01201

upstream raw materials:

cyclobutanemethanol

(S)-2-amino-3-cyclobutylpropanoic acid

di-tert-butyl dicarbonate

cyclobutylmethyl methanesulfonate

Downstream raw materials:

[2-cyclobutyl-1S-(methoxymethylcarbamoyl)ethyl]-carbamic acid tert-butyl ester