Water → HCID 58599399, compound

HRID 130481Notes

Reaction equation

HRID 130481 reaction equation
[O:1]=[C:2]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[CH:10][CH:9]=1)[CH2:3][S:4][C:5](=[O:7])[CH3:6].[OH-].[Li+].[C:31](Cl)(=O)[CH2:32][CH2:33]CC.O>CN(C=O)C.CCOC(C)=O>[O:1]=[C:2]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[CH:10][CH:9]=1)[CH2:3][S:4][C:5](=[O:7])[CH2:6][CH2:31][CH2:32][CH3:33]

Participants

7

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 61186Valeryl chlorideHCID 11430433HCID 11430433, compound

Product 1

HCID 58599399HCID 58599399, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Thioacetic acid S-{2-oxo-2-[4-(4-trifluoromethoxy-benzenesulfonylamino)-phenyl]-ethyl}ester (SI-4) (0.5 g, 1.15 mmol) was dissolved in anhydrous DMF (5 ml). Lithium hydroxide (28 mg, 1.15 mmol) was added and the solution was sonicated until homogeneous and heated to 90° C. for 4 hours. The solution was allowed to cool to room temperature and valeryl chloride (150 mg, 1.27 mmol) was added and the mixture stirred for 16 hours. The solution was partioned between 20 ml each water and EtOAc. The organic layer was washed with water, then brine and dried over Na2SO4. The solution was then filtered, stripped of solevent and the product purified by flash chromatography (100% DCM). The solvent was evaporated to afford 107 mg (0.22 mmol, 19%) product as a clear oil. 1H-NMR: (400 MHz, DMSO): 8.07 (d, 2H), 7.60 (d, 2H), 7.40 (d, 2H), 7.25 (d, 2H), 2.40 (s, 2H), 2.10 (t, 2H), 1.42 (t, 2H) 1.11 (t,2H), 0.09 (t, 3H); LC-MS (ES+): 476 [M]+ m/e.

Workup

  1. customthe solution was sonicated until homogeneous and
  2. temperatureto cool to room temperature
  3. washThe organic layer was washed with water
  4. dry with materialbrine and dried over Na2SO4
  5. filtrationThe solution was then filtered
  6. custompurified by flash chromatography (100% DCM)
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ca1ac77f6ed7413b85d1a956dfb6e76f
Source dataset
uspto-grants-2008_06
Patent number
US07381749B2

Reaction notes

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