Sodium Hydroxide → 1-(4-((3-(Azido(phenyl)methyl)phenoxy)methyl)phenyl)cyclopropanecarboxylic acid

HRID 332684Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of methyl 1-(4-((3-(azido(phenyl)methyl)phenoxy)methyl)-phenyl)cyclopropanecarboxylate (0.569 g, 1.375 mmol) in methanol (12.9 mL) and tetrahydrofuran (5.1 mL), was added 2M aqueous sodium hydroxide (12.9 mL). The reaction was stirred at 50° C. for 3 hours 30 minutes and then at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the pH was adjusted to pH4 using 2M aqueous hydrochloric acid with stirring. The mixture was extracted with dichloromethane (×3), and the combined organic extracts washed with brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure to afford the title compound (0.552 g, quantitative yield). The material was used directly in the next step with no further purification

Workup

waitat room temperature for 16 hours
concentrationThe reaction mixture was concentrated under reduced pressure
stirringwith stirring
extractionThe mixture was extracted with dichloromethane (×3)
washthe combined organic extracts washed with brine
dry with materialdried (magnesium sulfate)
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3b504a6e121b4b11b8ebfb6ae935e1e1
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877774B2

Reaction notes

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