Water → HCID 14994381, compound

HRID 846582Notes

Reaction equation

HRID 846582 reaction equation
[NH2:1][C:2]1[C:7]([C:8](OCC)=[O:9])=[C:6]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:5]([C:20]([O:22][CH3:23])=[O:21])=[C:4]([CH:24]([CH3:26])[CH3:25])[N:3]=1.O>C1(C)C=CC=CC=1.O1CCCC1>[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)[C:5]([C:20]([O:22][CH3:23])=[O:21])=[C:4]([CH:24]([CH3:26])[CH3:25])[N:3]=1

Participants

5

Reactant 2

HCID 962WaterHCID 14994380Amino-3-ethoxycarbonyl-4-(4-fluorophenyl)-6-isopropyl-5-methoxycarbonyl-pyridine

Product 1

HCID 14994381HCID 14994381, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
30 °C

Procedure

100 ml (0.35 mol) of a 3.5M solution of sodium bis-(2-methoxy-ethoxy)-dihydroaluminate in toluene are initially introduced under argon into 100 ml of tetrahydrofuran p.a. 63 g (175 mmol) of the compound from Example III dissolved in 700 ml of tetrahydrofuran are added dropwise and the mixture is subsequently stirred at 30° C. for 1 h. 2 l of water are cautiously added dropwise. The phases are separated and the aqueous phase is washed twice with 700 ml of ethyl acetate. The combined organic phases are washed with 500 ml of saturated sodium chloride solution and dried using sodium sulphate. The solution is filtered and concentrated in vacuo. The residue is chromatographed in a column (φ 6 cm) on 400 g of silica gel 230-400 mesh using petroleum ether/ethyl acetate (1:1). The eluate is concentrated in vacuo and the residue is thoroughly stirred in ether/petroleum ether.

Workup

  1. additionare added dropwise
  2. customThe phases are separated
  3. washthe aqueous phase is washed twice with 700 ml of ethyl acetate
  4. washThe combined organic phases are washed with 500 ml of saturated sodium chloride solution
  5. customdried
  6. filtrationThe solution is filtered
  7. concentrationconcentrated in vacuo
  8. customThe residue is chromatographed in a column (φ 6 cm) on 400 g of silica gel 230-400 mesh
  9. concentrationThe eluate is concentrated in vacuo
  10. stirringthe residue is thoroughly stirred in ether/petroleum ether

Sources & evidence

ORD record
ord-13bb54d256b045ba8d39f0f62e699e4b
Source dataset
uspto-grants-1992_08
Patent number
US05137881

Reaction notes

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