Water → [(1S)-5-(3-{[6-(4-ethylphenyl)-3-(trifluoromethyl)-2-pyridinyl]amino}propoxy)-2,3-dihydro-1H-inden-1-yl]acetic acid

To a solution of ethyl [(1S)-5-(3-{[6-(4-ethylphenyl)-3-(trifluoromethyl)-2-pyridinyl]amino}propoxy)-2,3-dihydro-1H-inden-1-yl]acetate (Example 317, 0.07 9, 0.09 mmol) in THF (2 mL), methanol (1 mL), and water (1 mL) was added LiOH (0.03 9, 1.37 mmol). The mixture was stirred at rt for 18 h, and then concentrated under reduced pressure. The residue was taken up in water and acidified to pH ˜5 using H3PO4 (a 5% aqueous solution). The aqueous solution was then extracted with EtOAc. The combined organic phases were dried (Na2SO4), filtered, and concentrated under reduced pressure to give the product (0.048 g, 71%). 1H NMR (400 MHz, CD2Cl2) δ 7.99 (d, 2H), 7.71 (d, 1H), 7.29 (d, 2H), 7.09 (dd, 2H), 6.81 (d, 1H), 6.73 (dd, 1H), 5.41 (b, 1H), 4.11 (t, 2H), 3.84 (q, 2H), 3.53 (qt, 1H), 2.95-2.70 (m, 5H), 2.52-2.38 (m, 2H), 2.20 (qt, 2H), 1.82-1.75 (m, 1H), 1.29 (m, 3H); LC-MS: RT=4.10 min, (M+H)+ 499.3.

1. concentrationconcentrated under reduced pressure
2. extractionThe aqueous solution was then extracted with EtOAc
3. dry with materialThe combined organic phases were dried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure

ORD record

ord-391f0b53a47b48909483ec2733f3428a

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07714004B2