Acetic Acid → HCID 10226143, compound

HRID 857339Notes

Reaction equation

HRID 857339 reaction equation
[Br:1][C:2]1[C:3]2[C:4]([S:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[C:5]3[CH:14]([CH2:15][C:16]([O:18]C)=[O:17])[CH2:13][CH2:12][N:6]3[C:7]=2[CH:8]=[C:9]([F:11])[CH:10]=1.C1COCC1.CO.[Li+].[OH-].CC(O)=O>[Cl-].[Na+].O>[Br:1][C:2]1[C:3]2[C:4]([S:20][C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)=[C:5]3[CH:14]([CH2:15][C:16]([OH:18])=[O:17])[CH2:13][CH2:12][N:6]3[C:7]=2[CH:8]=[C:9]([F:11])[CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 86594288HCID 86594288, compound

Product 1

HCID 10226143HCID 10226143, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of the ester of Step 9 (80 mg) in a 3:1 mixture of THF/MeOH (3 mL) at r.t. was added 1N LiOH (1 mL, aqueous solution). The reaction mixture was stirred at r.t. for 2 h and AcOH (0.5 mL) and brine (5 mL) were added. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 40% EtOAc/hexane containing 1% AcOH to provide 70 mg of the title compound as a pale yellow solid.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. washeluted with 40% EtOAc/hexane containing 1% AcOH

Sources & evidence

ORD record
ord-209d828a3346461c901fcb89c3489d22
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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