Hydrochloric Acid → HCID 22261118, compound

HRID 898446Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A sample of 2-methyl-2-[4-(2-{5-methyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-oxazol-4-yl}-ethoxy)-phenoxy]-propionic acid ethyl ester (55 mg, 0.103 mmol) was dissolved in 10 mL of EtOH with 3 mL of 5 N NaOH. This mixture was allowed to stir at 60° C. for 1 h. The mixture was cooled to room temperature and then acidified to pH 2 by the dropwise addition of 5 N HCl. This acidic mixture was diliuted with 10 mL of H2O and then extracted with CH2Cl2 (2×25 mL). The organic layers were combined, dried over NaCl, and solvent removed in vacuo which provided 49 mg (94%) of desired acid: 1H NMR (400 MHz, CDCl3) δ 8.32 (d, 2 H), 7.95 (d, 2 H), 6.82 (d, 2 H), 6.74 (d, 2 H), 4.35 (t, 2 H), 3.25 (t, 2 H), 2.50 (s, 3 H), 1.44 (s, 6 H), 1.32 (s, 12 H); MS (EI) 508.0 (M+H)+.

Workup

temperatureThe mixture was cooled to room temperature
extractionextracted with CH2Cl2 (2×25 mL)
dry with materialdried over NaCl, and solvent
customremoved in vacuo which

Sources & evidence

ORD record: ord-15dba9d631394ee3a55ffbf426c851e2
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351728B2

Reaction notes

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