Acetic Anhydride → HCID 18438968, compound

HRID 1393335Notes

Reaction equation

HRID 1393335 reaction equation
O[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([C:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:19][CH:20]=2)[N:15]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[C:14]=1[CH3:37])=[N:11][OH:12].CC([O-])=O.[Na+].CC(OC(C)=O)=O>CN(C=O)C.C(Cl)Cl>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]2[C:10]([C:13]3[C:21]4[C:16](=[CH:17][C:18]([O:22][C:23]([F:26])([F:24])[F:25])=[CH:19][CH:20]=4)[N:15]([S:27]([C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)(=[O:28])=[O:29])[C:14]=3[CH3:37])=[N:11][O:12][C:2]=2[CH:7]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 136251062HCID 136251062, compound

Product 1

HCID 18438968HCID 18438968, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 9 (3.8 g, 7.1 mmol) and NaOAc (3 eq, 1.8 g) in DMF (120 mL) was added Ac2O (3 eq, 2 mL). The reaction was heated to 110° C. for 4 hours at which time no starting material was detected by LC analysis. The reaction was cooled and diluted with DCM. The solution was washed with NH4Cl, brine and NaHCO3, then dried over Na2SO4 and concentrated. The residue was purified via flash chromatography eluding with 20% EtOAc/hexanes. Product was isolated as white foam.

Workup

  1. temperatureThe reaction was cooled
  2. washThe solution was washed with NH4Cl, brine and NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified via flash chromatography
  6. customProduct was isolated as white foam

Sources & evidence

ORD record
ord-8082da0c84664c5e8bdfa7f5fc80f5ad
Source dataset
uspto-grants-2008_03
Patent number
US07345085B2

Reaction notes

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