Acetic Anhydride → HCID 10773832, compound

HRID 2203312Notes

Reaction equation

HRID 2203312 reaction equation
[C:1](OC(=O)C)(=O)[CH3:2].[NH2:8]/[C:9](=[N:17]\[OH:18])/[CH:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12]>N1C=CC=CC=1>[CH3:1][C:2]1[O:18][N:17]=[C:9]([CH:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:8]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 133681488HCID 133681488, compound

Product 1

HCID 10773832HCID 10773832, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (4.6 mL, 49 mmol) was added to a pyridine (50 mL) solution of the intermediate from Step A (2.6 g, 16.2 mmol). The solution was heated at reflux for 1 hour and then at room temperature overnight. The solution was then concentrated to remove most of the pyridine. The concentrated solution was diluted with EtOAc and washed twice with water. The organic layer was concentrated and the residue purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated product. 1H NMR δ (ppm) (CHCl3-d): 4.19 (2H, dd, J=72, 3.6 Hz), 3.94 (1H, m, J=7.3 Hz), 2.58 (3H, s), 1.60 (3H, t, 7.3 Hz), 1.25 (3H, t, J=7.1 Hz). m/z=185.1 (M+H).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 1 hour
  3. customat room temperature
  4. customovernight
  5. concentrationThe solution was then concentrated
  6. customto remove most of the pyridine
  7. additionThe concentrated solution was diluted with EtOAc
  8. washwashed twice with water
  9. concentrationThe organic layer was concentrated
  10. customthe residue purified by silica gel chromatography
  11. customto give the indicated product

Sources & evidence

ORD record
ord-08e5e3ab672a401ea2ca72afa1a832db
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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