Ethyl 2-bromopropionate → Piperidin-1-yl-acetic acid

Temperature

70 °C

Ethyl 2-bromopropionate (0.0001 mol) was added to a mixture of intermediate (12) (0.000084 mol) and tri-n-butylthiourea (TBTU) (0.000168 mol) in DIPEA (4 ml). The reaction mixture was shaken for 2 hours at 70° C. The reaction mixture was cooled to room temperature, filtered and the filtrate was evaporated. The residue was dissolved in DCM (4 ml), then washed with water (2 ml). The mixture was filtered through Extrelut™ and the filter residue was washed with DCM (2×3 ml). The filtrate was evaporated. The residue was purified by HPLC (Waters column, with Xterra MS C18; eluent: [(0.5% NH4OAc in H2O)/CH3CN 90/10)]/CH3CN (0 min) 85/15, (10 min) 10/90, (16 min) 0/100, (18.10-20.00 min) 85/15), yielding 1-piperidineacetic acid, α-phenyl-4-[4-[[[4′-(trifluoromethyl)[1,1′-biphenyl]-2-yl]carbonyl]amino]phenyl]-, 2-ethoxy-1-methyl-2-oxoethyl ester (compound 111).

1. temperatureThe reaction mixture was cooled to room temperature
2. filtrationfiltered
3. customthe filtrate was evaporated
4. dissolutionThe residue was dissolved in DCM (4 ml)
5. washwashed with water (2 ml)
6. filtrationThe mixture was filtered through Extrelut™
7. washthe filter residue was washed with DCM (2×3 ml)
8. customThe filtrate was evaporated
9. customThe residue was purified by HPLC (Waters column

ORD record

ord-44f300cc2e9f47e988b009f58ede8876

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07642378B2