Chloroform → HCID 68605042, compound

Temperature

0 °C

To an ice cooled solution of 3,5-difluorophenylacetic acid (2.16 g) in anhydrous dichloromethane (100 mL) under nitrogen was added HOBt-hydrate (4.23 g), EDAC-HC1 (3.6 g), and NMM (2.2 mL). The reaction mixture was stirred at 0° C. under nitrogen for 15 min and L-serine methyl ester-HCl (1.96 g) was added followed by NMM (1.38 mL). The reaction was stirred at 0° C. for 1 H and RT for 2 H. The reaction mixture was concentrated in vacuo and partitioned between water (100 mL) and ethyl acetate (125 mL). The organic phase was collected and consecutively washed with water, dilute aqueous sodium bicarbonate, brine, dried, filtered and the solvent removed in vacuo to yield a white solid. Trituration with CHCl3 afforded pure title compound (1.8 g). The impure filtrate was subjected to flash chromatography (20% acetone/CHCl3) to afford additional title compound (800 mg, total yield 76%). 1H NMR (300 MHz, d6-DMSO) δ3.57 (d, 2H), 3.62(s, 3H), 3.7 (m, 1H), 4.35, (m, 1H), 5.1 (bs, 1H), 7.00 (d, 2H), 7.09 (t, 1H), 8.53, (d, 1H). MS APCI, m/z=274 (M+1). LC/MS: 1.34 min.

1. stirringThe reaction was stirred at 0° C. for 1 H and RT for 2 H
2. concentrationThe reaction mixture was concentrated in vacuo
3. custompartitioned between water (100 mL) and ethyl acetate (125 mL)
4. customThe organic phase was collected
5. washconsecutively washed with water, dilute aqueous sodium bicarbonate, brine
6. customdried
7. filtrationfiltered
8. customthe solvent removed in vacuo
9. customto yield a white solid

ORD record

ord-deb78789bbe24c90ad8d4e49c3418dfd

Source dataset

uspto-grants-2007_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07294622B2