Hydrochloric Acid → HCID 58136548, compound

HRID 877264Notes

Reaction equation

O.[OH-].[Li+].[CH3:4][CH:5]([CH3:43])[CH:6]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][N:30]2[C:35](=[O:36])[CH2:34][O:33][C:32]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[N:31]2)=[CH:25][CH:24]=1)[C:7]([NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH2:12][CH:13]([C:19]([O:21]C)=[O:20])[CH2:14]2)=[O:8].Cl>C1COCC1.O>[CH3:4][CH:5]([CH3:43])[CH:6]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][N:30]2[C:35](=[O:36])[CH2:34][O:33][C:32]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[N:31]2)=[CH:25][CH:24]=1)[C:7]([NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH2:12][CH:13]([C:19]([OH:21])=[O:20])[CH2:14]2)=[O:8]

Participants

Conditions

Temperature: 60 °C

Procedure

26 mg (0.63 mmol) of lithium hydroxide monohydrate were added to a solution of 170 mg (0.32 mmol) of methyl 4-[(3-methyl-2-{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}butanoyl)amino]-2,3-dihydro-1H-indene-2-carboxylate (Example 134A) in 11 ml of THF and 11 ml of water, and the mixture was stirred at 60° C. for 12 h. The reaction mixture was then adjusted to pH 2 with 1 M hydrochloric acid and extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulfate and then concentrated to dryness under reduced pressure. This gave 141 mg (content 98%, 0.26 mmol, 84% of theory) of the title compound as a mixture of isomers.

Workup

extractionextracted twice with ethyl acetate
dry with materialThe combined organic phases were dried over magnesium sulfate
concentrationconcentrated to dryness under reduced pressure
additionThis gave 141 mg (content 98%, 0.26 mmol, 84% of theory) of the title compound as a mixture of isomers

Sources & evidence

ORD record: ord-1d83dfbea4bb49f4a8b947e89d6406f5
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987256B2

Reaction notes

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