Lithium Hydroxide → 3-(3-(((2'-(Butyloxy)-2-methyl-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)propanoic acid

HRID 1662317Notes

Reaction equation

[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][O:21][C:22]2[CH:23]=[C:24]([CH2:28][CH2:29][C:30]([O:32]C)=[O:31])[CH:25]=[CH:26][CH:27]=2)=[CH:16][C:15]=1[CH3:34])[CH2:2][CH2:3][CH3:4].[Li+].[OH-]>C1COCC1.CO>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][O:21][C:22]2[CH:23]=[C:24]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH:25]=[CH:26][CH:27]=2)=[CH:16][C:15]=1[CH3:34])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of 4.3 (0.0241 g, 0.0521 mmol) in THF/MeOH (2/1) (1.5 mL) was added LiOH (0.50 mL, 0.500 mmol). The resulting mixture was stirred overnight at 23° C., quenched with excess 1N HCl, and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The crude residue was purified by combiflash (0 to 40% EtOAc/hexanes) to afford 4 (0.0166 g, 71.0% yield). MS ESI (neg.) m/e: 393.1 (M−H)+. 1H NMR (400 MHz, CDCl3) δ ppm 7.32 (1H, s), 7.20-7.29 (4H, m), 6.83-6.92 (5H, m), 6.74 (1H, d, J=2.9 Hz), 5.07 (2H, s), 3.83 (2H, t, J=6.6 Hz), 3.79 (3H, s), 2.97 (2H, t, J=7.8 Hz), 2.68-2.73 (2H, m), 2.19 (3H, s), 1.53-1.60 (2H, m), 1.22-1.31 (2H, m), 0.83 (3H, t, J=7.3 Hz).

Workup

customquenched with excess 1N HCl
extractionextracted with EtOAc
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated
customThe crude residue was purified by combiflash (0 to 40% EtOAc/hexanes)

Sources & evidence

ORD record: ord-3de60160211245ee9c062e70e5c32527
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Reaction notes

Loading…