4-Toluenesulfonyl chloride → (S)-2-((tert-Butoxycarbonyl)amino)-3-phenylpropyl 4-methylbenzenesulfonate

Temperatur

0 °C

The recovered intermediate (20a) (8.5 g, 33 mmol, 1.0 eq) was dissolved into 70 mL pyridine containing potassium hydroxide (2.1 g, 37 mmol, 1.1 eq) and the mixture was chilled in an ice bath. Tosyl chloride (7.1 g, 37 mmol, 1.1 eq) was added and the mixture was stirred at 0° C. for 2 hours then refrigerated overnight. The mixture was filtered and the filtrate was concentrated under reduced pressure. The recovered residue was dissolved into 300 mL EtOAc, washed with 2×200 mL 1M H3PO4, saturated bicarbonate, and saturated aqueous NaCl. The organic was dried over MgSO4 and concentrated under reduced pressure to yield intermediate (20b) (10.3 g) as a pale brown oil.

1. temperaturethe mixture was chilled in an ice bath
2. waitthen refrigerated overnight
3. filtrationThe mixture was filtered
4. concentrationthe filtrate was concentrated under reduced pressure
5. dissolutionThe recovered residue was dissolved into 300 mL EtOAc
6. washwashed with 2×200 mL 1M H3PO4, saturated bicarbonate, and saturated aqueous NaCl
7. dry with materialThe organic was dried over MgSO4
8. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-97dd494bc26541f79491a8a3347188b0

Quelldatensatz

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08013005B2