Acetic Anhydride → HCID 20094381, compound

HRID 273866Notes

Reaction equation

HRID 273866 reaction equation
C(OC([N:8]([CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][CH2:37][CH3:38])[CH:9]([CH3:26])[CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[C:18]([C:20]([NH2:22])=[O:21])[CH:19]=1)[N:16]([CH2:23][CH2:24][OH:25])[CH2:15][CH2:14]2)=O)(C)(C)C.C(N(CC)CC)C.[C:46](OC(=O)C)(=[O:48])[CH3:47]>C(Cl)Cl>[C:46]([O:25][CH2:24][CH2:23][N:16]1[C:17]2[C:13](=[CH:12][C:11]([CH2:10][CH:9]([NH:8][CH2:27][CH2:28][O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH2:37][CH3:38])[CH3:26])=[CH:19][C:18]=2[C:20]([NH2:22])=[O:21])[CH2:14][CH2:15]1)(=[O:48])[CH3:47]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 20094345HCID 20094345, compound

Product 1

HCID 20094381HCID 20094381, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]-1-(2-hydroxyethyl)indoline-7-carboxamide (60 mg) in methylene chloride (3 ml) were added triethylamine (24 μl) and acetic anhydride (13 μl) with stirring under ice cooling, and the mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure and to the concentrate was added water. The mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium bicarbonate solution and water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was dissolved in methylene chloride (2 ml). To the solution was added trifluoroacetic acid (0.5 ml), the mixture was stirred at room temperature for 30 minutes, and the reaction mixture was concentrated under reduced pressure. To the concentrate was added a saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of chloroform and methanol (7/1) as eluent to give 41 mg of 1-(2-acetoxyethyl)-5-[2-[2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carboxamide as an oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure and to the concentrate
  3. additionwas added water
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous sodium bicarbonate solution and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. dissolutionthe residue was dissolved in methylene chloride (2 ml)
  9. additionTo the solution was added trifluoroacetic acid (0.5 ml)
  10. stirringthe mixture was stirred at room temperature for 30 minutes
  11. concentrationthe reaction mixture was concentrated under reduced pressure
  12. additionTo the concentrate was added a saturated aqueous sodium bicarbonate solution
  13. extractionthe mixture was extracted with ethyl acetate
  14. washThe extract was washed with water
  15. dry with materialdried over anhydrous magnesium sulfate
  16. customThe solvent was evaporated under reduced pressure
  17. customthe residue was purified by medium pressure liquid column chromatography on silica gel using
  18. additiona mixture of chloroform and methanol (7/1) as eluent

Sources & evidence

ORD record
ord-7ea8ef7d01af45eb948a6786c5a61f1d
Source dataset
uspto-grants-1995_02
Patent number
US05387603

Reaction notes

Loading…