Acetic Acid → 4-amino-3-(2-(benzyloxy)ethyl)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

HRID 20700Notes

Reaction equation

HRID 20700 reaction equation
C([O-])(=O)C.[NH4+:5].[CH2:6]([O:13][CH2:14][CH2:15][C:16]1[C:17](=[O:35])[O:18][C:19]2[C:24]([C:25]=1O)=[CH:23][CH:22]=[C:21]([O:27][CH3:28])[C:20]=2[O:29][CH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(O)(=O)C.C1(C)C=CC=CC=1>O>[NH2:5][C:25]1[C:24]2[C:19](=[C:20]([O:29][CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[C:21]([O:27][CH3:28])=[CH:22][CH:23]=2)[O:18][C:17](=[O:35])[C:16]=1[CH2:15][CH2:14][O:13][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 517165Ammonium AcetateHCID 866181373-(2-(benzyloxy)ethyl)-8-(cyclopentyloxy)-4-hydroxy-7-methoxy-2H-chromen-2-one

Product 1

HCID 866181384-amino-3-(2-(benzyloxy)ethyl)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ammonium acetate (27.7 g, 360 mmol) was added to a solution of 3-(2-(benzyloxy)ethyl)-8-(cyclopentyloxy)-4-hydroxy-7-methoxy-2H-chromen-2-one (5 g, 12 mmol), acetic acid (25 mL), and toluene (100 mL). The reaction was refluxed with the water being removed using a Dean-Stark apparatus. After 2 h, the toluene was removed by distillation. After an additional 5 h at reflux, the reaction was allowed to cool to rt, poured into cold water (100 mL), and then extracted with ethyl acetate (100 mL×3). The combined extracts were washed with sat'd NaHCO3 (100 mL×4) and then brine (50 mL×3), filtered, concentrated, and purified by silica gel chromatography (ethyl acetate:petroleum ether) to give 4-amino-3-(2-(benzyloxy)ethyl)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one: MS (ESI): 410.

Workup

  1. customremoved
  2. customthe toluene was removed by distillation
  3. temperatureAfter an additional 5 h at reflux
  4. additionpoured into cold water (100 mL)
  5. extractionextracted with ethyl acetate (100 mL×3)
  6. washThe combined extracts were washed with sat'd NaHCO3 (100 mL×4)
  7. filtrationbrine (50 mL×3), filtered
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography (ethyl acetate:petroleum ether)

Sources & evidence

ORD record
ord-0999915fd0ea431784776419a1d0d277
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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