ChemicalBook CAS DataBase List ETHYL METHYLPHOSPHONIC ACID

ETHYL METHYLPHOSPHONIC ACID synthesis

7synthesis methods

Product Name:ETHYL METHYLPHOSPHONIC ACID
CAS Number:1832-53-7
Molecular formula:C3H9O3P
Molecular Weight:124.08

591-22-0
310 suppliers
$11.19/25ML

5284-09-3
1 suppliers
inquiry

53123-88-9 Synthesis

53123-88-9
754 suppliers
$9.00/10mg

1832-53-7
41 suppliers
$96.90/1g

Yield:-

Reaction Conditions:

with sodium hydrogencarbonate in dichloromethane;ethyl acetate

Steps:

1 Methyl-phosphonic acid ethyl ester C-43 rapamycin ester
Methyl-phosphonic acid ethyl ester C-43 rapamycin ester To a cooled (0° C.) solution of rapamycin (0.1 g, 0.109 mmol) in 1.5 mL of dichloromethane was added a solution of 3,5-lutidine (0.088 g, 0.82 mmol) in 0.25 mL of dichloromethane, under an atmosphere of N₂, followed immediately by a solution of ethyl methylphosphonochloridate (0.078 g, 0.547 mmol) in 0.25 mL of dichloromethane. The colorless reaction solution was stirred at 0° C. for 3 h (reaction monitored by MS; reaction sample diluted directly with 50:50CH₃CN/H₂O, 1 drop DMSO, prior to analysis). The cold (0° C.) reaction solution was diluted with ~20 mL EtOAc then transferred to a separatory funnel containing EtOAc (150 mL) and saturated NaHCO₃ (100 mL). Upon removing the aqueous layer, the organic layer was washed successively with ice cold 1N HCl (1*100 mL), saturated NaHCO₃ (1*100 mL), and brine (1*100 mL), then dried over MgSO4 and concentrated. The crude product was purified by silica gel flash chromatography (eluted with 0.5:10:3:3 MeOH/DCM/EtOAc/hexane) to provide 0.024 g of a white solid (~2:1 diastereomeric mixture): ¹H NMR (300 MHz, CDCl₃) d 4.19 (m, 1 Ha, 1 Hb), 4.15-4.01 (m, 3 Ha, 3 Hb), 1.56-1.27 (m, 6 Ha, 6 Hb); ³¹P NMR (121 MHz, CDCl₃) d 32.1, 29.9; 1043 m/z (M+Na).

References:

Berstein, David L.;Metcalf III, Chester A.;Rozamus, Leonard W.;Wang, Yihan US2003/220297, 2003, A1

64-17-5 Synthesis