Sodium Hydroxide → HCID 9915561, compound

HRID 348280Notes

Reaction equation

C([O:3][C:4](=[O:43])[C:5]([CH3:42])([O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:23]=[C:24]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH:25]=[CH:26][CH:27]=3)[O:19][C:20]=2[CH3:21])=[CH:9][CH:8]=1)C.[OH-].[Na+]>CO>[F:34][C:31]1[CH:32]=[CH:33][C:28]([C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([C:18]3[O:19][C:20]([CH3:21])=[C:16]([CH2:15][CH2:14][O:13][C:10]4[CH:11]=[CH:12][C:7]([CH2:6][C:5]([CH3:42])([O:35][C:36]5[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=5)[C:4]([OH:43])=[O:3])=[CH:8][CH:9]=4)[N:17]=3)[CH:23]=2)=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 55 °C

Procedure

3-(4-{2-[2-(4′-Fluorobiphenyl-3-yl)-5-methyloxazol-4-yl]ethoxy}phenyl)-2-methyl-2-phenoxypropionic acid ethyl ester (3.6 mmol) in MeOH (7 mL) was treated with 2N NaOH (7 mL) and warmed to 55° C. After 18 h, the mixture was concentrated under reduced pressure and then acidified with 5N HCl to pH=1. The solution was extracted with EtOAc and then the organic phases dried (Na2SO4), filtered and concentrated to a white solid. 1H NMR (400 MHz, CDCl3) δ 8.18, (s, 1H), (d, J=7.6 Hz, 1H), 7.62–7.58 (m, 3H),7.48 (t, J=7.6 Hz, 1H), 7.24–7.03 (m, 7H), 6.90 (t, J=8.4 Hz, 2H), 6.83 (t, J=8.4 Hz, 2H), 4.22 (t, J=6.8 Hz, 2H), 3.25 (d, J=14.0 Hz, 1H), 3.15 (d, J=14.0 Hz, 1H), 3.01 (t, J=6.8 Hz, 2H), 2.40 (s, 3H), 1.42 (s, 3H); MS (EI) 552.3 (M+H)+, 550.3 (M−H)−.

Workup

concentrationthe mixture was concentrated under reduced pressure
extractionThe solution was extracted with EtOAc
dry with materialthe organic phases dried (Na2SO4)
filtrationfiltered
concentrationconcentrated to a white solid

Sources & evidence

ORD record: ord-346c0be668e54fb2ac9dc04ac8047264
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176224B2

Reaction notes

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