Lithium Hydroxide → HCID 25056792, compound

HRID 2101792Notes

Reaction equation

HRID 2101792 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])=[CH:9][C:8]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C@H:28]([CH2:34][CH2:35][CH3:36])[CH2:29][C:30]([O:32]C)=[O:31])=[CH:24][C:23]=2[CH3:37])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[Li+].[OH-]>C1COCC1.CO>[CH3:4][C:2]([C:5]1[C:10]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])=[CH:9][C:8]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C@H:28]([CH2:34][CH2:35][CH3:36])[CH2:29][C:30]([OH:32])=[O:31])=[CH:24][C:23]=2[CH3:37])=[CH:7][CH:6]=1)([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57672401HCID 57672401, compound

Product 1

HCID 25056792HCID 25056792, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 27.5 (0.039 g, 0.076 mmol) in THF/MeOH (2/1) (1.5 mL) was added LiOH (0.50 mL, 0.50 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 and concentrated. The crude residue was purified by silica gel chromatography (0 to 40% EtOAc/hexanes) to afford a 27 (0.024 g, 64% yield). MS ESI (neg.) m/e: 491.2 (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. concentrationconcentrated
  5. customThe crude residue was purified by silica gel chromatography (0 to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6bf3cd127fea4d2cae77e6e704fa40b5
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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