Aldoxime → HCID 69828738, compound

HRID 1839254Notes

Reaction equation

HRID 1839254 reaction equation
[CH:1]1([NH:6][C:7]2[N:15]=[CH:14][N:13]=[C:12]3[C:8]=2[N:9]=[CH:10][N:11]3[C@H:16]2[C@@H:20]3[O:21][C:22]([CH3:25])([CH3:24])[O:23][C@@H:19]3[C@@H:18]([C:26](O)=[O:27])[O:17]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(OC1C=C[C:39]2[C:34](=CC=CC=2)[N:33]1C(OCC)=O)C.C(=[N:49]O)C>C(COC)OC>[CH3:24][C:22]1([CH3:25])[O:23][C@H:19]2[C@@H:18]([C:26]3[O:27][N:33]=[C:34]([CH3:39])[N:49]=3)[O:17][C@@H:16]([N:11]3[CH:10]=[N:9][C:8]4[C:12]3=[N:13][CH:14]=[N:15][C:7]=4[NH:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[C@@H:20]2[O:21]1

Participants

5

Reactant 3

HCID 7863AldoximeHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 18336833HCID 18336833, compound

Product 1

HCID 69828738HCID 69828738, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
22 °C

Procedure

A mixture of (3aS,4S,6R,6aR)-6-(6-cyclopentylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (0.2 g), 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (146 mg), acetaldoxime (76 mg) and dimethoxyethane (DME, 25 ml) was heated under reflux for 4 days and then cooled to 22° C. The mixture was concentrated in vacuo and ethyl acetate (40 ml) added to the residue. The resulting suspension was washed with 0.5M citric acid solution (3×20 ml) and the aqueous washings were extracted with ethyl acetate (2×20 ml). The combined organic extracts were washed with water (20 ml) and brine (30 ml) and dried (MgSO4). After concentration in vacuo the residue was purified by chromatography on silica gel, eluting with ethyl acetate:cyclohexane (1:1), to give the title compound (63 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 days
  3. concentrationThe mixture was concentrated in vacuo and ethyl acetate (40 ml)
  4. additionadded to the residue
  5. washThe resulting suspension was washed with 0.5M citric acid solution (3×20 ml)
  6. extractionthe aqueous washings were extracted with ethyl acetate (2×20 ml)
  7. washThe combined organic extracts were washed with water (20 ml) and brine (30 ml)
  8. dry with materialdried (MgSO4)
  9. concentrationAfter concentration in vacuo the residue
  10. customwas purified by chromatography on silica gel
  11. washeluting with ethyl acetate:cyclohexane (1:1)

Sources & evidence

ORD record
ord-9ed2fdfd3714445daef5ae103a3241f3
Source dataset
uspto-grants-2004_01
Patent number
US06677316B2

Reaction notes

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