Chlorotrimethylsilane → HCID 18650356, compound

Mix trifluoroacetic acid (30 mL) with acetonitrile (10 mL) and add, by dropwise addition, to an ice-cold solution of N-(9-phenylfluorenyl)-3(S)-[(diethoxyphosphinyl)acetyl]piperidine-2(R)-carboxylic acid, tert-butyl ester (3.5 g, 5.8 mmol) in acetonitrile (40 mL) and water (4 mL). Stir for 15 minutes, warm to room temperature and stir for an additional hour. Pour into saturated aqueous sodium hydrogen carbonate (500 mL) and extract into ethyl acetate (3×200 mL). Evaporate to a residue and take up the residue in acetonitrile (20 mL) and methylene chloride (20 mL). Place under a nitrogen atmosphere and add trimethylsilyl chloride (5 mL, 35 mmol). Stir overnight then add water. Stir for 15 minutes then blow to a residue with a stream of dry nitrogen. Take up the residue in water (100 mL) and wash with toluene (5×100 mL). Freeze dry to give a residue. Take up the residue in methanol (10 mL) and isopropanol (5 mL). Add propylene oxide (5 mL) and filter to give the title compound.

1. stirringstir for an additional hour
2. extractionextract into ethyl acetate (3×200 mL)
3. customEvaporate to a residue
4. stirringStir overnight
5. stirringStir for 15 minutes
6. washwash with toluene (5×100 mL)
7. customFreeze dry
8. customto give a residue
9. filtrationAdd propylene oxide (5 mL) and filter

ORD record

ord-812be162cb374e7fbf96a3117044e353

Source dataset

uspto-grants-1993_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05194430