Stannous Chloride → 3-(2-Chloro-4-methoxycarbonylmethyl-phenyl)-3-oxo-propionic acid tert-butyl ester

A flame-dried flask is charged with tert-butyl-diazoacetate (0.62 mL, 4.48 mmol) and anhydrous tin(II) chloride (168 mg, 0.88 mmol) in dry DCM (10 mL). (3-Chloro-4-formyl-phenyl)-acetic acid methyl ester 14 (500 mg, 2.35 mmol) is dissolved in DCM (5 mL) and added dropwise to the reaction mixture. After stirring for 6 h at room temperature the reaction mixture is poured into brine (50 mL) and extracted with ether (3×50 mL). The combined organic layers are dried (MgSO4), filtered, concentrated and purified on reverse phase HPLC (H2O/MeCN gradient) to afford 3-(2-Chloro-4-methoxycarbonylmethyl-phenyl)-3-oxo-propionic acid tert-butyl ester 56 as a white solid: MS calculated for C16H19Cl2NaO5 (M+Na+) 349.1, found 349.1.

1. additionadded dropwise to the reaction mixture
2. extractionextracted with ether (3×50 mL)
3. dry with materialThe combined organic layers are dried (MgSO4)
4. filtrationfiltered
5. concentrationconcentrated
6. custompurified on reverse phase HPLC (H2O/MeCN gradient)

ORD-Eintrag

ord-f918d03da3d3488db19f7cfa0a76c7c2

Quelldatensatz

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07820705B2