Sodium Hydroxide → HCID 22261124, compound

HRID 1609957Notes

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-0bc2d3784a794a00b0dee18b7f695a76
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982278B2

Reaction notes

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