Lithium Hydroxide → HCID 25056535, compound

HRID 2101783Notes

Reaction equation

HRID 2101783 reaction equation
[CH:1]1([C@H:4]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:19]=[C:20]([C:28]4[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:29]=4[F:36])[C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:22][CH:23]=3)=[CH:12][CH:11]=2)[CH2:5][C:6]([O:8]C)=[O:7])[CH2:3][CH2:2]1.[Li+].[OH-]>C1COCC1.CO>[CH:1]1([C@@H:4]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:19]=[C:20]([C:28]4[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:29]=4[F:36])[C:21]([C:24]([CH3:25])([CH3:26])[CH3:27])=[CH:22][CH:23]=3)=[CH:12][CH:11]=2)[CH2:5][C:6]([OH:8])=[O:7])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57672377HCID 57672377, compound

Product 1

HCID 25056535HCID 25056535, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 22.1 (0.040 g, 0.082 mmol) in THF/MeOH (2/1) (1.5 mL) was added a 1 M solution of LiOH (0.50 mL, 0.500 mmol). The resulting mixture was stirred overnight at 23° C., quenched with excess 1 N HCl, and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography (0 to 40% EtOAc/hexanes) to afford a 22 (0.019 g, 50% yield). MS ESI (neg.) m/e: 475.3 (M−H)+.

Workup

  1. customquenched with excess 1 N HCl
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (0 to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c7007cfdaeb74a50a0f3b11718b9c570
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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