Triphenylphosphine → (R)-methyl 2-(5-bromo-2-nitrophenoxy)propanoate

Temperatur

0 °C

Triphenylphosphine (624.0 mg, 2.38 mmol) was added at room temperature to a solution of 5-bromo-2-nitrophenol A-15 (400.0 mg, 1.83 mmol) and methyl(−)—(S)-lactate (0.149 mL, 1.56 mmol) in anhydrous methylene chloride (18.3 mL) under an atmosphere of argon. After 10 mins of stirring, the reaction mixture was cooled to 0° C. and diisopropyl azodicarboxylate (0.360 mL, 1.83 mmol) was added dropwise. The orange solution was warmed to room temperature, stirred for 12 h, then concentrated to ca. 1.0 mL, diluted with pentane (7 mL) and diethyl ether (8 mL), filtered and rinsed with diethyl ether-pentane (15 mL). The filtrate was concentrated to dryness under reduced pressure, and the residue was purified by flash column chromatography on silica gel (hexanes to ethyl acetate gradient) to give (R)-methyl 2-(5-bromo-2-nitrophenoxy)propanoate (R)-A-16 as a yellow solid (525.0 mg; Yield=94%). MS (ESI) [M+1]+ 304, 306.

1. temperatureThe orange solution was warmed to room temperature
2. stirringstirred for 12 h
3. concentrationconcentrated to ca. 1.0 mL
4. additiondiluted with pentane (7 mL) and diethyl ether (8 mL)
5. filtrationfiltered
6. washrinsed with diethyl ether-pentane (15 mL)
7. concentrationThe filtrate was concentrated to dryness under reduced pressure
8. customthe residue was purified by flash column chromatography on silica gel (hexanes to ethyl acetate gradient)

ORD-Eintrag

ord-07f67dc4f9ac450db22ece8a29052c24

Quelldatensatz

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08637507B2