Acetic Acid → HCID 10864624, compound

HRID 1596047Notes

Reaction equation

HRID 1596047 reaction equation
C([N:8]([CH2:29][C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]=1Br)[S:9]([C:12]1[CH:17]=[CH:16][C: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)=[CH:14][CH:13]=1)(=[O:11])=[O:10])(OC(C)(C)C)=O.[C:41]([Li])([CH3:44])([CH3:43])[CH3:42].C[C:47]([OH:49])=[O:48]>C1COCC1>[F:26][C:25]([F:28])([F:27])[O:24][C:21]1[CH:20]=[CH:19][C:18]([C:15]2[CH:16]=[CH:17][C:12]([S:9]([NH:8][CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:31]=3[C:47]([O:49][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:48])(=[O:10])=[O:11])=[CH:13][CH:14]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11104175HCID 11104175, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 10864624HCID 10864624, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 9D (1.50 g, 2.36 mmol) in THF (25 mL) under N2 at −78° C. was added tert-butyllithium (1.7 M in pentane, 3.0 mL, 5.10 mmol). The resulting reddish-purple solution was stirred for 30 minutes at the same temperature and then quenched with HOAc (0.56 mL, 9.77 mmol) and warmed to RT. The solvent was removed and the resulting oil was dissolved in ethyl acetate (100 mL), washed with H2O and brine, dried (Na2SO4), filtered, and concentrated. Purification on silica gel with a gradient of 10% hexanes/CH2Cl2 to 3% ethyl acetate/CH2Cl2 provided 1.13 g (86%) of the desired compound as a white foam.

Workup

  1. customThe solvent was removed
  2. dissolutionthe resulting oil was dissolved in ethyl acetate (100 mL)
  3. washwashed with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification on silica gel with a gradient of 10% hexanes/CH2Cl2 to 3% ethyl acetate/CH2Cl2

Sources & evidence

ORD record
ord-a97d75e69cea4286895d2d76c7c16c86
Source dataset
uspto-grants-2001_09
Patent number
US06288261B1

Reaction notes

Loading…