Triethylamine → N-[(4-fluorophenyl)sulfonyl]-D-valine

Temperature

0 °C

To a solution of D-valine (6.40 g, 54.6 mmol) in H2O (62 mL) and acetone (25 mL) was added triethylamine (16.2 mL, 117 mmol). The solution was cooled to zero degrees C. in an ice/H2O bath and a solution of 4-fluorobenzenesulfonyl chloride (10.0 g, 51.4 mmol) in acetone (25 mL) was added dropwise. After stirring at room temperature for 20 hours, the resulting yellow solution was concentrated in vacuo to remove the acetone. The aqueous residue was extracted with toluene (2×50 mL) and acidified to pH=1 with 12 M HCl. The solution was extracted with ethyl acetate (3×50 mL) and the combined organic layers were washed successively with 1M KHSO4 (50 mL), H2O (50 mL), and sat'd NaCl (50 mL), then dried over MgSO4. Concentration in vacuo and trituration with hexane afforded N-[(4-fluorophenyl)-sulfonyl]-D-valine as a white solid (12.56 g, 89%): MS MH+ calcd. for Anal. Calc'd for C11H14NO4SF: C, H, N. Found: C, H, N. HR mass calculated for C11H14NO4S: 276.0706. Found: 276.0710.

1. concentrationthe resulting yellow solution was concentrated in vacuo
2. customto remove the acetone
3. extractionThe aqueous residue was extracted with toluene (2×50 mL)
4. extractionThe solution was extracted with ethyl acetate (3×50 mL)
5. washthe combined organic layers were washed successively with 1M KHSO4 (50 mL), H2O (50 mL), and sat'd NaCl (50 mL)
6. dry with materialdried over MgSO4
7. concentrationConcentration in vacuo and trituration with hexane

ORD record

ord-9547ea42b2224e208166f5a9338acea6

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06087359