Hydrochloric Acid → 2-{2'-[(Acetyl-ethyl-amino)-methyl]-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl}-2-methyl-propionic acid

HRID 563607Notes

Reaction equation

C([O:3][C:4](=[O:33])[C:5]([C:8]1[CH:9]=[C:10]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:17]=2[CH2:26][N:27]([C:30](=[O:32])[CH3:31])[CH2:28][CH3:29])[C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)([CH3:7])[CH3:6])C.[OH-].[Na+].C(Cl)Cl.Cl>C1COCC1.CCO>[C:30]([N:27]([CH2:26][C:17]1[CH:18]=[C:19]([C:22]([F:23])([F:25])[F:24])[CH:20]=[CH:21][C:16]=1[C:10]1[C:11]([O:14][CH3:15])=[CH:12][CH:13]=[C:8]([C:5]([CH3:6])([CH3:7])[C:4]([OH:33])=[O:3])[CH:9]=1)[CH2:28][CH3:29])(=[O:32])[CH3:31]

Participants

Conditions

Temperature: 50 °C

Procedure

To 2-{2′-[(acetyl-ethyl-amino)-methyl]-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl}-2-methyl-propionic acid ethyl ester (0.290 g, 0.63 mmol) in THF (2.6 mL) and EtOH (2 mL) was added 1N aqueous NaOH (1.9 mL), and the reaction was stirred at 50° C. overnight. Analytical LCMS indicated that starting material was still present, so additional 1N aqueous NaOH (1 mL) was added, and the reaction was stirred at 70° C. for 2 hours. Additional 1N aqueous NaOH (1 mL) was added, and the reaction was stirred for another 6 hours. The mixture was worked-up with CH2Cl2 and 1N aqueous HCl, and the organic layer was dried over Na2SO4, decanted, and concentrated. The residue was purified by preparative HPLC to give the title compound. M+H is 438.

Workup

stirringthe reaction was stirred at 70° C. for 2 hours
stirringthe reaction was stirred for another 6 hours
dry with materialthe organic layer was dried over Na2SO4
customdecanted
concentrationconcentrated
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-9ed8e40f60a3401ba0d81312d6ec1402
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067445B2

Reaction notes

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