Acetic Anhydride → HCID 59191399, compound

HRID 1023958Notes

Reaction equation

HRID 1023958 reaction equation
[NH2:1][CH2:2][CH:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][C:17]=3[OH:24])=[C:11]([F:25])[CH:10]=2)[CH2:4]1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>ClCCl.O>[CH2:22]([C:19]1[CH:20]=[CH:21][C:16]([O:15][C:12]2[CH:13]=[CH:14][C:9]([N:5]3[CH2:4][CH:3]([CH2:2][NH:1][C:26](=[O:28])[CH3:27])[O:7][C:6]3=[O:8])=[CH:10][C:11]=2[F:25])=[C:17]([OH:24])[CH:18]=1)[CH3:23]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 59191317HCID 59191317, compound

Product 1

HCID 59191399HCID 59191399, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-Aminomethyl-3-[4-(4-ethyl-2-hydroxyphenoxy)-3-fluorophenyl]-oxazolidin-2-one (10 mg, 0.028 mmol) in 2 ml of dry dichloromethane, cooled to 0° C., was added acetic anhydride (3 mg, 0.028 mmol) taken in 0.2 ml of dichloromethane. The reaction mixture was warmed to rt and stirred for 5 minutes until reaction was complete on TLC. The reaction mixture was diluted with 3 ml of water and the layers separated. The aqueous layer was extracted with dichloromethane and the combined organic fraction was dried over anhydrous Na2SO4 and concentrated. The crude residue obtained was purified by preparative HPLC (Column: C18 Symmetry (300×19 mm), 7μ, Mobile phase A: 20 mM ammonium acetate, Mobile phase B: Acetonitrile) to get 6 mg, 55.2% of the title compound.

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. dry with materialthe combined organic fraction was dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe crude residue obtained
  6. customwas purified by preparative HPLC (Column: C18 Symmetry (300×19 mm), 7μ, Mobile phase A: 20 mM ammonium acetate, Mobile phase B: Acetonitrile)

Sources & evidence

ORD record
ord-938c0d3c6fd04b328f31a984d577aec3
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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