Pyridine → HCID 70872018, compound

HRID 470704Notes

Reaction equation

HRID 470704 reaction equation
[C:1]([O:4][CH2:5][CH2:6][NH:7][CH2:8][C@H:9]1[O:14][CH2:13][C@H:12]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:10]1)(=[O:3])[CH3:2].[C:23](OC(=O)C)(=[O:25])[CH3:24].N1C=CC=CC=1>ClCCl.[Cl-].[Na+].O>[C:1]([O:4][CH2:5][CH2:6][N:7]([C:23](=[O:25])[CH3:24])[CH2:8][C@H:9]1[O:14][CH2:13][C@H:12]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:10]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 70871763HCID 70871763, compound

Product 1

HCID 70872018HCID 70872018, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The compound (264 mg, 0.83 mmol) obtained in Step 4 above was dissolved in dichloromethane (8 ml), acetic anhydride (0.50 ml, 5.30 mmol) was added and the resulting mixture was stirred at room temperature for 1 hour. Then pyridine (0.10 ml, 1.24 mmol) was added and the resulting mixture was further stirred for 1 hour. Saturated brine (20 ml) was added to the reaction mixture and the resulting mixture was stirred for 1 hour, followed by extraction with dichloromethane. The organic layer was washed with saturated sodium bicarbonate solution and brine in that order and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography [chloroform:methanol=40:1 (v/v)] to give 244 mg (82%) of the title compound as a colorless amorphous solid.

Workup

  1. stirringthe resulting mixture was further stirred for 1 hour
  2. stirringthe resulting mixture was stirred for 1 hour
  3. extractionfollowed by extraction with dichloromethane
  4. washThe organic layer was washed with saturated sodium bicarbonate solution and brine in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue obtained
  8. customwas purified by silica gel column chromatography [chloroform:methanol=40:1 (v/v)]

Sources & evidence

ORD record
ord-1e6a311049834cf396d6fdaa09e64754
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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