Sodium Hydroxide → 3-{4-[2-(2-Biphenyl-4-yl-5-methyl-oxazol-4-yl)ethoxy]-phenyl}-2-methyl-2-phenoxypropionic acid

HRID 348270Notes

Reaction equation

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

Participants

Conditions

Temperature: 55 °C

Procedure

3-{4-[2-(2-Biphenyl-4-yl-5-methyl-oxazol-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 (7%). MS [EI+] 534 (M+H)+, 566 (M+Na)+, [EI−] 532 (M−H)+; HPLC: T=3.29 min, purity 99%.

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 (7%)
customT=3.29 min, purity 99%

Sources & evidence

ORD record: ord-c4cfb9c330e94c3eaa85daf9799aadd8
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176224B2

Reaction notes

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