Acetic Acid → HCID 10300920, compound

HRID 857373Notes

Reaction equation

HRID 857373 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][CH:5]1[C:9]2=[C:10]([S:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[C:11]3[C:12]([CH:25]([CH3:27])[CH3:26])=[CH:13][C:14]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6]1.CC(O)=O>C1COCC1.CO.[Li+].[OH-]>[CH2:18]([O:17][C:14]1[CH:13]=[C:12]([CH:25]([CH3:27])[CH3:26])[C:11]2[C:10]([S:28][C:29]3[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=3)=[C:9]3[CH:5]([CH2:4][C:3]([OH:36])=[O:2])[CH2:6][CH2:7][N:8]3[C:16]=2[CH:15]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 131726148HCID 131726148, compound

Product 1

HCID 10300920HCID 10300920, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of the ester of Step 5 100 mg in THF/MeOH (3/1) mixture at r.t. was added in LiOH aqueous solution 1.0 mL. The reaction mixture was stirred at r.t. for 1 hour then 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 70 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-fb90bc7301bf4b11aa51da2aac3fb39e
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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