Lithium Hydroxide → HCID 69308244, compound

HRID 1880569Notes

Reaction equation

HRID 1880569 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[CH2:19][CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][CH:22]=1.[Li+].[OH-]>C1COCC1.CO.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:12][CH:13]=2)=[CH:4][C:3]=1[CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69307065HCID 69307065, compound

Product 1

HCID 69308244HCID 69308244, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
45 °C

Procedure

To a THF/MeOH/water solution (ca. 40 mL/40 mL/10 mL) of the intermediate from Step F (8.53 g, 17.84 mmol) was added LiOH (3.66 g, 89.2 mmol). The solution was stirred at 45° C. until no starting material remained by HPLC (ca. 2 hrs). The solution was concentrated to remove the majority of MeOH/THF and then partitioned between aqueous 1N HCl and ethyl acetate. The organic phase was washed with water (2×), brine and dried over Na2SO4. The solution was filtered and concentrated to give the title compound. The crude material was use in the next step without purification.

Workup

  1. customremained by HPLC (ca. 2 hrs)
  2. concentrationThe solution was concentrated
  3. customto remove the majority of MeOH/THF
  4. custompartitioned between aqueous 1N HCl and ethyl acetate
  5. washThe organic phase was washed with water (2×), brine
  6. dry with materialdried over Na2SO4
  7. filtrationThe solution was filtered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e8733e65d7a74972b7e8f3e9db8f2b37
Source dataset
uspto-grants-2012_11
Patent number
US08318760B2

Reaction notes

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