2-tert-Butyl-4-(methoxycarbonyl)-1,3-oxazolidine-3-carboxylate

Base Information

• Chemical Name: 2-tert-Butyl-4-(methoxycarbonyl)-1,3-oxazolidine-3-carboxylate
• CAS No.: 145625-08-7
• Molecular Formula: C14H25 N O5
• Molecular Weight: 287.356
• DSSTox Substance ID: DTXSID50703312
• Mol file: 145625-08-7.mol

Synonyms:DTXSID50703312;AKOS030241532;2-tert-Butyl-4-(methoxycarbonyl)-1,3-oxazolidine-3-carboxylate

Chemical Property of 2-tert-Butyl-4-(methoxycarbonyl)-1,3-oxazolidine-3-carboxylate

Chemical Property:

• PSA: 65.07000
• LogP: 2.10540
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 230.10284761
• Heavy Atom Count: 16
• Complexity: 291

Purity/Quality:

97% ^*data from raw suppliers

(2R,4S)-3-tert-Butyl 4-methyl-2-tert-butyloxazolidine-3,4-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1N(C(CO1)C(=O)OC)C(=O)[O-]

Technology Process of 2-tert-Butyl-4-(methoxycarbonyl)-1,3-oxazolidine-3-carboxylate

There total 6 articles about 2-tert-Butyl-4-(methoxycarbonyl)-1,3-oxazolidine-3-carboxylate 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%

di-tert-butyl dicarbonate (24424-99-5) + methyl (2R,4S)-2-(tert-butyl)-1,3-oxazolane-4-carboxylate (93250-89-6,93250-90-9) → (2R,4S)-2-tert-butyloxazolidinone-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester (145625-08-7)

Guidance literature:

With sodium hydrogencarbonate; In methanol; at 50 ℃; for 5h;

DOI:10.1016/j.tet.2004.06.085

Reference yield: 85.0%

di-tert-butyl dicarbonate (24424-99-5) + (2RS,5S)-2-(tert-butyl)-5-methoxycarbonyl-1,3-oxazolidine (190080-34-3) → (2R,4S)-2-tert-butyloxazolidinone-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester (145625-08-7)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 12h; Ambient temperature;

DOI:10.1016/S0040-4039(97)00364-X

Reference yield:

t-butylglyoxal (4480-47-1) → (2R,4S)-2-tert-butyloxazolidinone-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester (145625-08-7)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / pentane / 72 h / 55 °C / Dean Stark conditions

2: sodium hydrogencarbonate / methanol / 18 h / 50 °C / Inert atmosphere

With sodium hydrogencarbonate; triethylamine; In methanol; pentane;

DOI:10.1021/ol203300k

upstream raw materials:

L-serin

di-tert-butyl dicarbonate

(2RS,5S)-2-(tert-butyl)-5-methoxycarbonyl-1,3-oxazolidine

methyl (2R,4S)-2-(tert-butyl)-1,3-oxazolane-4-carboxylate

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