Lithium Hydroxide → HCID 58277404, compound

HRID 1949246Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:11]=[C:10]([C:20]([O:22]CC)=[O:21])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Li+]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]([C:13]3[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=3)[N:11]=[C:10]([C:20]([OH:22])=[O:21])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

23.9 g (72.8 mmol) of the compound of Example 40A are provided in 100 ml of 1,4-dioxane, 100 ml (200 mmol) of a 2N solution of lithium hydroxide in water are added, and the mixture is stirred at 50° C. for 1 h. The mixture is concentrated, the residue is diluted with water, a conc. aqueous hydrogen chloride solution is subsequently added until the pH is acidic, the mixture is extracted with dichloromethane, and the organic phase is dried over magnesium sulfate, filtered and concentrated. The residue is stirred in a little diethyl ether, collected by filtration and dried under high vacuum. 22.0 g (100% of theory) of the title compound are obtained.

Workup

concentrationThe mixture is concentrated
additionthe residue is diluted with water
additiona conc. aqueous hydrogen chloride solution is subsequently added until the pH
extractionthe mixture is extracted with dichloromethane
dry with materialthe organic phase is dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
stirringThe residue is stirred in a little diethyl ether
filtrationcollected by filtration
customdried under high vacuum

Sources & evidence

ORD record: ord-9f675896e04242b0b6bfeb7cd8e4250e
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399682B2

Reaction notes

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