Sodium Hydroxide → HCID 58074531, compound

HRID 877253Notes

Reaction equation

[OH-].[Na+].[F:3][C:4]([F:34])([F:33])[CH:5]([CH3:32])[CH:6]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]2[C:24](=[O:25])[CH2:23][O:22][C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:20]2)=[CH:14][CH:13]=1)[C:7]([O:9]CC)=[O:8]>O1CCOCC1>[F:34][C:4]([F:3])([F:33])[CH:5]([CH3:32])[CH:6]([C:12]1[CH:13]=[CH:14][C:15]([CH2:18][N:19]2[C:24](=[O:25])[CH2:23][O:22][C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:20]2)=[CH:16][CH:17]=1)[C:7]([OH:9])=[O:8]

Participants

Conditions

Temperature: 80 °C

Procedure

11.4 ml (11.4 mmol) of 1 N aqueous sodium hydroxide solution were added to a solution of 1283 mg (2.86 mmol) of ethyl 4,4,4-trifluoro-3-methyl-2-{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}butanoate in 10 ml of dioxane, and the mixture was stirred at 80° C. overnight. After the reaction had gone to completion, the dioxane was removed under reduced pressure and the solution that remained was diluted with water and then adjusted to pH 2 using 1 M hydrochloric acid. The precipitated solid was filtered off, washed with water and dried under reduced pressure at 45° C. overnight. This gave 1058 mg (2.52 mmol, 88% of theory) of the title compound as a mixture of isomers.

Workup

customthe dioxane was removed under reduced pressure
additionthe solution that remained was diluted with water
filtrationThe precipitated solid was filtered off
washwashed with water
customdried under reduced pressure at 45° C. overnight
additionThis gave 1058 mg (2.52 mmol, 88% of theory) of the title compound as a mixture of isomers

Sources & evidence

ORD record: ord-deb839b213244d4c8218c8622af6ec75
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987256B2

Reaction notes

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