Acetic Acid → HCID 10184165, compound

HRID 857366Notes

Reaction equation

HRID 857366 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][CH:5]1[C:9]2=[C:10]([S:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[C:11]3[C:12]([CH:21]([CH3:23])[CH3:22])=[CH:13][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6]1.[Li+].[OH-].CC(O)=O>C1COCC1.CO>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([S:24][C:10]2[C:11]3[C:12]([CH:21]([CH3:23])[CH3:22])=[CH:13][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:15][C:16]=3[N:8]3[CH2:7][CH2:6][CH:5]([CH2:4][C:3]([OH:32])=[O:2])[C:9]=23)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 131726146HCID 131726146, compound

Product 1

HCID 10184165HCID 10184165, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of the ester of Step 4 (140 mg) in THF/MeOH (3/1) mixture at r.t. was added 1 M LiOH (aqueous solution). The reaction mixture was stirred at r.t. for 2 hours and AcOH was added and the solvent was evaporated. The residue was taken up in EtOAc/H2O and the organic phase was washed with brine, dried (MgSO4), filtered and evaporated. The residue was purified by silica gel chromatography eluting with 1% AcOH in EtOAc to give 100 mg of the title compound.

Workup

  1. customthe solvent was evaporated
  2. washthe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 1% AcOH in EtOAc

Sources & evidence

ORD record
ord-03163b9954f34f2685f950872d3d041e
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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