Hydrochloric Acid → HCID 49806253, compound

HRID 1615058Notes

Reaction equation

[CH:1]1([C:4]2[CH:40]=[CH:39][C:7]([CH2:8][O:9][C:10]3[CH:15]=[CH:14][C:13]([CH:16]4[CH2:19][N:18]([C:20]([C:22]5[CH:27]=[C:26]([O:28][CH2:29][C@H:30]6[CH2:34][O:33]C(C)(C)[O:31]6)[CH:25]=[CH:24][N:23]=5)=[O:21])[CH2:17]4)=[CH:12][C:11]=3[O:37][CH3:38])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.Cl.[OH-].[Na+]>O1CCCC1>[CH:1]1([C:4]2[CH:40]=[CH:39][C:7]([CH2:8][O:9][C:10]3[CH:15]=[CH:14][C:13]([CH:16]4[CH2:17][N:18]([C:20]([C:22]5[CH:27]=[C:26]([O:28][CH2:29][C@H:30]([OH:31])[CH2:34][OH:33])[CH:25]=[CH:24][N:23]=5)=[O:21])[CH2:19]4)=[CH:12][C:11]=3[O:37][CH3:38])=[CH:6][CH:5]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of {{3-[4-(4-cyclopropylbenzyloxy)-3-methoxyphenyl]azetidin-1-yl}-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)pyridin-2-yl]-methanone prepared in (1) (0.27 g) in THF (4.0 mL) was added 1 N hydrochloric acid (2.0 mL). The reaction mixture was stirred at 60° C. for 2 hr. To the reaction mixture was added aqueous 1 N NaOH (2.0 mL) and the mixture was extracted with ethyl acetate. The solvent was removed under reduced pressure. A mixed solvent of hexane/ethyl acetate (1/1) was added to the residue. The precipitated solid was collected on a filter and dried to give the title compound (0.23 g, 93%).

Workup

extractionthe mixture was extracted with ethyl acetate
customThe solvent was removed under reduced pressure
additionA mixed solvent of hexane/ethyl acetate (1/1) was added to the residue
customThe precipitated solid was collected on
filtrationa filter
customdried

Sources & evidence

ORD record: ord-c624839e3d4f46949f68ee900f377380
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765739B2

Reaction notes

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