Hydrochloric Acid → (S)-3-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenoxy)propane-1,2-diol

HRID 1172942Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of (R)-3-(3-chloro-4-isopropoxyphenyl)-5-(4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-1,2,4-oxadiazole (0.339 g, 0.762 mmol) in THF (15.24 ml) was added a solution of 1N HCl (1.524 ml, 1.524 mmol). After 48 h additional 1N HCl (2.286 ml, 2.286 mmol) was added and the reaction mixture was heated to 70° C. for about 2 h. After cooling to ambient temperature a solution of 1N NaOH (3.81 ml, 3.81 mmol) was added and the reaction mixture was concentrated in vacuo. The resulting solid was washed with copious amounts of water and dried in vacuo to provide (S)-3-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenoxy)propane-1,2-diol (0.294 g, 94%) as a colorless solid. LCMS (Table 1, Method c) Rt=2.73 min, m/z 405 (M+H)+.

Workup

additionwas added
concentrationthe reaction mixture was concentrated in vacuo
washThe resulting solid was washed with copious amounts of water
customdried in vacuo

Sources & evidence

ORD record: ord-d1cab83a427d40c6a899c880e292b9cb
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834039B2

Reaction notes

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