Acetic Anhydride → HCID 89740538, compound

HRID 1485834Notes

Reaction equation

HRID 1485834 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:22][CH2:23][NH2:24])=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>C(N(CC)CC)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:22][CH2:23][NH:24][C:25](=[O:27])[CH3:26])=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 117903247HCID 117903247, compound

Product 1

HCID 89740538HCID 89740538, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

80 mg, 0.25 mmol of 29 was added to a 25 mL oven-dried flask containing 5 mL freshly distilled DCM, under argon atmosphere. Acetic anhydride (21 μL, 0.22 mmol) and triethyl amine (35 μL) were then added to the solution and the resultant mixture stirred at room temperature for 3 h. The reaction mixture was then quenched by addition of saturated ammonium chloride, and extracted into DCM. The combined organic layers were dried (Na2SO4) and concentrated to a crude mixture, which was purified by column chromatography (Silica gel, 3:1 hexane:EtOAc) to give the desired product.

Workup

  1. customoven-dried flask
  2. additioncontaining 5 mL freshly distilled DCM
  3. customThe reaction mixture was then quenched by addition of saturated ammonium chloride
  4. extractionextracted into DCM
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated to a crude mixture, which
  7. customwas purified by column chromatography (Silica gel, 3:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-bd0d3f04b24c4ca18c329651e98ccd26
Source dataset
uspto-grants-2016_08
Patent number
US09422320B2

Reaction notes

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