Sodium Hydroxide → HCID 22261124, compound

HRID 898459Notes

Reaction equation

C([O:3][C:4](=[O:34])[CH2:5][O:6][C:7]1[C:12]([CH2:13][CH2:14][CH3:15])=[CH:11][C:10]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:9][C:8]=1[CH2:31][CH2:32][CH3:33])C.[OH-].[Na+]>C1COCC1.CO>[CH3:24][C:23]1[O:22][C:21]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[N:20][C:19]=1[CH2:18][CH2:17][O:16][C:10]1[CH:9]=[C:8]([CH2:31][CH2:32][CH3:33])[C:7]([O:6][CH2:5][C:4]([OH:34])=[O:3])=[C:12]([CH2:13][CH2:14][CH3:15])[CH:11]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of {4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-2,6-dipropyl-phenoxy}-acetic acid ethyl ester (244 mg, 0.524 mmol) in THF (3 mL) and MeOH (6 mL) was treated with 2.5N aqueous NaOH (2 mL). The solution was heated at 55° C. for 2.5 h, cooled to ambient temperature, and concentrated in vacuo. The residue was treated with ice water (1 mL) and acidified with 5N aqueous HCl (2 mL). The mixture with CH2Cl2 (3 mL) was transferred to a ChemElute cartridge (5 g) and eluted with CH2Cl2 (40 mL). The eluent was concentrated to a white foam (228 mg, 100%): 1H NMR (400 MHz, CDCl3) δ 0.94 (t, 6H, J=7.3 Hz), 1.60 (sextet, 4H, J=7.6 Hz), 2.37 (s, 3H), 2.50-2.54 (m, 4H), 2.98 (brt, 2H), 4.19 (brt, 2H), 4.37 (s, 2H), 6.56 (s, 2H), 7.42-7.43 (m, 3H), 7.98-7.99 (m, 2H); MS (ES) m/e 438.2 [M+1].

Workup

temperaturecooled to ambient temperature
concentrationconcentrated in vacuo
additionThe residue was treated with ice water (1 mL)
washeluted with CH2Cl2 (40 mL)
concentrationThe eluent was concentrated to a white foam (228 mg, 100%)

Sources & evidence

ORD record: ord-8d32b10572af4734acf0f4668a22ff23
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351728B2

Reaction notes

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