Lithium Hydroxide → HCID 86685886, compound

HRID 1629793Notes

Reaction equation

[F:1][C:2]1([F:39])[C:7]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[CH:14][CH:13]=2)([C:8]([F:11])([F:10])[F:9])[NH:6][C:5](=[O:26])[C:4]([C:27]([O:29]CC)=[O:28])=[C:3]1[C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=1.[Li+].[OH-]>CO>[F:39][C:2]1([F:1])[C:7]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][C:22]([F:24])([F:25])[F:23])=[CH:14][CH:13]=2)([C:8]([F:9])([F:10])[F:11])[NH:6][C:5](=[O:26])[C:4]([C:27]([OH:29])=[O:28])=[C:3]1[C:32]1[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of Intermediate 103H (100 mg, 0.177 mmol) in MeOH (2 mL) was added 2 M LiOH (0.4 mL, 0.800 mmol). The resulting mixture was stirred at 100° C. for 15 min. LC-MS indicated the product to be the major component along with a trace amount of SM and 14% of the corresponding methyl ester. 2 M LiOH (100 uL) was then added and the reaction was stirred at 100° C. for an additional 15 min. The reaction was concentrated, acidified with 1 N HCl, and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated to yield the desired product (75 mg, 78%) as a solid. LCMS Anal. Calc'd for C24H19F8NO4 537.12, found [M+H] 537.9.

Workup

stirringthe reaction was stirred at 100° C. for an additional 15 min
concentrationThe reaction was concentrated
extractionextracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-646300cfe62748e9ae3e0bb4bee3656a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791091B2

Reaction notes

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