Water → 5-[3-(4-Chloro-2-methyl-phenyl)-3-(3-fluoro-4-hydroxy-phenyl)-propionyl]-1-methyl-1H-pyridin-2-one

HRID 1617889Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([O:26]C(C)C)=[C:22]([F:30])[CH:21]=2)[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=[O:11])=[C:4]([CH3:31])[CH:3]=1.B(Cl)(Cl)Cl.O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([F:30])[CH:21]=2)[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=[O:11])=[C:4]([CH3:31])[CH:3]=1

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of 5-[3-(4-Chloro-2-methyl-phenyl)-3-(3-fluoro-4-isopropoxy-phenyl)-propionyl]-1-methyl-1H-pyridin-2-one (example 323, step 4, 1.969 g) in dichloromethane (32.5 mL) was cooled to −10° C. At this temperature boron trichloride solution (1 M in dichloromethane, 13.4 mL) was slowly added. The reaction mixture was stirred at −10° C. for 1 h. The crude reaction mixture was poured into water/sat. sodium hydrogencarbonate-solution, extracted 3× with ethyl acetate, the organic layers were washed 2× with water, dried over magnesium sulfate and concentrated in vacuo to give the title compound as a light yellow solid, MS (ESI−): m/z=397.9 [M−H]−.

Workup

customThe crude reaction mixture
extractionsodium hydrogencarbonate-solution, extracted 3× with ethyl acetate
washthe organic layers were washed 2× with water
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0516a8e35b6146b393150cc532379690
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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