(2R,4S)-N-Benzyl-2-t-butyloxazolidine-4-carboxylic Acid, Methyl Ester

Base Information

• Chemical Name: (2R,4S)-N-Benzyl-2-t-butyloxazolidine-4-carboxylic Acid, Methyl Ester
• CAS No.: 145451-89-4
• Molecular Formula: C16H23NO3
• Molecular Weight: 277.36
• DSSTox Substance ID: DTXSID40447793
• Nikkaji Number: J1.283.079C
• Wikidata: Q82266684
• Mol file: 145451-89-4.mol

Synonyms:145451-89-4;(2R,4S)-N-Benzyl-2-t-butyloxazolidine-4-carboxylic Acid, Methyl Ester;Methyl (2R,4S)-3-benzyl-2-tert-butyl-1,3-oxazolidine-4-carboxylate;4-Oxazolidinecarboxylic acid, 2-(1,1-dimethylethyl)-3-(phenylmethyl)-, methyl ester, (2R-cis)- (9CI);DTXSID40447793;ZTAOHROUZKWTRP-DZGCQCFKSA-N;AKOS030241108;J-008106;(2R,4S)-N-Benzyl-2-tert-butyloxazolidine-4-carboxylic acid,methyl ester;(2R)-2alpha-tert-Butyl-3-benzyloxazolidine-4alpha-carboxylic acid methyl ester

Chemical Property of (2R,4S)-N-Benzyl-2-t-butyloxazolidine-4-carboxylic Acid, Methyl Ester

Chemical Property:

• Vapor Pressure: 7.12E-05mmHg at 25°C
• Boiling Point: 343.3°C at 760 mmHg
• Flash Point: 161.4°C
• PSA: 38.77000
• Density: 1.096g/cm³
• LogP: 2.37050
• Solubility.: Acetone, Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 277.16779360
• Heavy Atom Count: 20
• Complexity: 331

Purity/Quality:

98%Min ^*data from raw suppliers

(2R,4S)-N-Benzyl-2-t-butyloxazolidine-4-carboxylicAcid,MethylEster ^*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)CC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)[C@@H]1N([C@@H](CO1)C(=O)OC)CC2=CC=CC=C2

Technology Process of (2R,4S)-N-Benzyl-2-t-butyloxazolidine-4-carboxylic Acid, Methyl Ester

There total 2 articles about (2R,4S)-N-Benzyl-2-t-butyloxazolidine-4-carboxylic Acid, 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:

benzaldehyde (100-52-7) → (2R,4S)-3-Benzyl-2-tert-butyl-oxazolidine-4-carboxylic acid methyl ester (145451-89-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₃N / methanol / 3 h / 0 °C

1.2: 85 percent / NaBH₄

2.1: p-TsOH / toluene / 4 h / Heating

With toluene-4-sulfonic acid; triethylamine; In methanol; toluene;

DOI:10.1016/S0040-4039(01)01631-8

Reference yield:

(S)-N-benzylserine methyl ester (123639-56-5) + pivalaldehyde (630-19-3) → (2R,4S)-3-Benzyl-2-tert-butyl-oxazolidine-4-carboxylic acid methyl ester (145451-89-4) + (2S,4S)-3-Benzyl-2-tert-butyl-oxazolidine-4-carboxylic acid methyl ester

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 4h; Heating;

DOI:10.1016/S0040-4039(01)01631-8

Reference yield: 97.0%

(2R,4S)-3-Benzyl-2-tert-butyl-oxazolidine-4-carboxylic acid methyl ester (145451-89-4) → ((2R,4R)-3-Benzyl-2-tert-butyl-oxazolidin-4-yl)-methanol (393867-18-0)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(01)01631-8

upstream raw materials:

(S)-N-benzylserine methyl ester

pivalaldehyde

benzaldehyde

Downstream raw materials:

(2R,4R)-3-Benzyl-4-[(S)-((2R,4S)-3-benzyl-2-tert-butyl-oxazolidin-4-yl)-hydroxy-methyl]-2-tert-butyl-oxazolidine-4-carboxylic acid methyl ester

((2R,4R)-3-Benzyl-2-tert-butyl-oxazolidin-4-yl)-methanol

(2R,4S)-3-Benzyl-2-tert-butyl-oxazolidine-4-carbaldehyde