Acetic Anhydride → HCID 18438968, compound

HRID 1864737Notes

Reaction equation

HRID 1864737 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 eluting 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. washeluting with 20% EtOAc/hexanes
  7. customProduct was isolated as white foam

Sources & evidence

ORD record
ord-4254a77ee1a047fcb7e2eeaaaf66e5ed
Source dataset
uspto-grants-2009_12
Patent number
US07625933B2

Reaction notes

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