Lithium Hydroxide → HCID 70818201, compound

HRID 2405947Notes

Reaction equation

HRID 2405947 reaction equation
[CH3:1][C@@:2]([S:24]([CH3:27])(=[O:26])=[O:25])([CH2:8][CH2:9][N:10]1[CH:14]=[C:13](B2OC(C)(C)C(C)(C)O2)[CH:12]=[N:11]1)[C:3]([O:5]CC)=[O:4].Br[C:29]1[CH:34]=[CH:33][C:32]([C:35]2[O:36][CH:37]=[CH:38][N:39]=2)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Li+]>CO.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C@@:2]([S:24]([CH3:27])(=[O:25])=[O:26])([CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[O:36][CH:37]=[CH:38][N:39]=3)=[CH:31][CH:30]=2)[CH:12]=[N:11]1)[C:3]([OH:5])=[O:4]

Participants

8

Reactant 4

HCID 3939Lithium HydroxideHCID 11430Potassium CarbonateHCID 110750322-(4-Bromophenyl)oxazoleHCID 70856732HCID 70856732, compound

Product 1

HCID 70818201HCID 70818201, compoundYield 64.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butanoate (0.2 g, 0.5 mmol) in MeOH (2.5 mL) in a microwave reactor vial was added 2-(4-bromophenyl)-1,3-oxazole (0.118 g, 0.525 mmol, 1.05 eq), potassium carbonate (0.214 g, 1.5 mmol, 3 eq), and palladium tetrakis (0.117 g, 0.1 mmol, 0.2 eq). The reaction mixture was irradiated at 120° C. in a microwave reactor for five minutes. The vial was allowed to cool to RT, and a solution of lithium hydroxide (0.036 g, 1.5 mmol, 3 eq) in water (2 mL) was added. The reaction mixture was allowed to stir at room temperature for one hour. The mixture was then washed with ethyl acetate (100 mL) and 1M sodium hydroxide (50 mL). The aqueous layer was separated and acidified to pH 1 with 6M HCl. The aqueous layer was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated to give (2R)-2-methyl-2-(methylsulfonyl)-4-{4-[4-(1,3-oxazol-2-yl)phenyl]-1H-pyrazol-1-yl}butanoic acid (0.125 g, 64% yield) as a white solid. LC-MS M+H+390.1.

Workup

  1. customThe reaction mixture was irradiated at 120° C. in a microwave reactor for five minutes
  2. washThe mixture was then washed with ethyl acetate (100 mL) and 1M sodium hydroxide (50 mL)
  3. customThe aqueous layer was separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f1c0e2d0544a4b18816e8f2b967807b7
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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