Hydrochloric Acid → HCID 66699089, compound

HRID 1095992Notes

Reaction equation

C[O:2][C:3](=[O:34])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:32])[C:18]([OH:31])([C:23]3[CH:24]=[N:25][C:26]([O:29]C)=[CH:27][CH:28]=3)[C:19]([F:22])([F:21])[F:20])=[C:13]([Cl:33])[CH:12]=2)=[CH:6][CH:5]=1.Cl>O1CCOCC1>[Cl:33][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=1[CH:17]([CH3:32])[C:18]([OH:31])([C:23]1[CH:28]=[CH:27][C:26](=[O:29])[NH:25][CH:24]=1)[C:19]([F:20])([F:22])[F:21])[O:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:34])=[O:2])=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-{3-chloro-4-[3,3,3-trifluoro-2-hydroxy-2-(6-methoxy-pyridin-3-yl)-1-methyl-propyl]-phenoxy}-benzoic acid methyl ester (22 mg) in dioxane (0.65 ml) was added conc. aqueous HCl (88 mg). The mixture was stirred at 100° C. for 1 h. The mixture was concentrated to dryness. The residue was dissolved in tetrahydrofuran (0.1 ml) and methanol (0.1 ml). 2 M aqueous NaOH solution (0.22 ml) was added and the mixture was stirred at room temperature for 2 h. The mixture was acidified with 2 M aqueous HCl. The organic solvents were evaporated. The precipitate was filtered, washed with water and dried to give the title compound as a colorless solid (15 mg). MS (m/e, ISP neg. ion)=466.0 [M−H+].

Workup

concentrationThe mixture was concentrated to dryness
dissolutionThe residue was dissolved in tetrahydrofuran (0.1 ml)
addition2 M aqueous NaOH solution (0.22 ml) was added
stirringthe mixture was stirred at room temperature for 2 h
customThe organic solvents were evaporated
filtrationThe precipitate was filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-7bfa7aa79b6a4d728abafc8079761fe8
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138189B2

Reaction notes

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