ChemicalBook CAS DataBase List N-P-TOSYLGLYCINE BENZYL ESTER

N-P-TOSYLGLYCINE BENZYL ESTER synthesis

7synthesis methods

Product Name:N-P-TOSYLGLYCINE BENZYL ESTER
CAS Number:63366-76-7
Molecular formula:C16H17NO4S
Molecular Weight:319.38

2462-31-9 Synthesis

2462-31-9
263 suppliers
$5.00/1g

98-59-9 Synthesis

98-59-9
592 suppliers
$9.00/5g

63366-76-7
21 suppliers
$106.00/1g

Yield:63366-76-7 86%

Reaction Conditions:

with sodium carbonate in dichloromethane at 20;Cooling with ice;

Steps:

General procedure: Syntheses of G(2-4) and P(2-4): General experimental procedure is as follows: Glycine or L-phenyl alanine derivative (as HCl salt) (10 mmol) and Na2CO3 (2.1 g, 20 mmol) were dissolved in anhydrous dichloromethane (50 mL) and cooled in an ice bath before tosyl chloride (1.9 g, 10 mmol) was added. The resultant reaction mixture was stirred overnight at room temperature. After the reaction, more solvent was added and the residue was washed sequentially with 0.1 M HCl, saturated NaHCO3 and brine. Organic portion was dried with Na2SO4 and concentrated in vacuo to give crude product. The product was purified by column chromatography on silica with hexane and EtOAc (1:1). Compound G3: Yield 86% as white solid. 1H NMR (400 MHz, CDCl3): δ 7.73 (d, J= 8.3 Hz, 2H, ArH), 7.37-7.23 (m, 7H, ArH), 5.05 (s, 2H, -OCH2-), 5.02 (broad singlet, 1H, -NH-), 3.82 (d, J= 5.5 Hz, 2H, -NCH2-), 2.42 (s, 3H, -CH3) ppm. 13C NMR (100 MHz, CDCl3): δ 168.8, 144.0, 136.3, 134.8, 129.9, 129.8, 128.8, 128.4, 127.4, 67.7, 44.3, 21.7 ppm. Anal. Calcd [C16H17NO4S]: C, 60.17; H, 5.37; N, 4.39; S, 10.04 Found: C, 59.61; H, 5.79; N, 4.73;S, 9.34.

References:

Fidan, Ismail;Salmas, Ramin Ekhteiari;Arslan, Mehmet;?entürk, Murat;Durdagi, Serdar;Ekinci, Deniz;?entürk, Esra;Co?gun, Sedat;Supuran, Claudiu T. [Bioorganic and Medicinal Chemistry,2015,vol. 23,# 23,p. 7353 - 7358]