Water → HCID 9822360, compound

HRID 2226937Notes

Reaction equation

HRID 2226937 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH2:22][CH2:23][NH:24][OH:25])[CH:17]=3)[C:12]2=[O:26])=[CH:4][CH:3]=1.C[Si]([N:31]=[C:32]=[O:33])(C)C.O>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH2:22][CH2:23][N:24]([C:32]([NH2:31])=[O:33])[OH:25])[CH:17]=3)[C:12]2=[O:26])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70696Trimethylsilyl isocyanateHCID 15227739HCID 15227739, compound

Product 1

HCID 9822360HCID 9822360, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-[3-(4-fluorophenyl)-propyl]-6-[2-(N-hydroxyamino)ethoxy]-1-oxo-1,2,3,4-tetrahydroisoquinoline (3.0 g, 8.4 mmol) in dioxane (100 mL) is added trimethylsilyl isocyanate (1.06 g, 9.2 mmol). The reaction is stirred at room temperature for 24 hours and subsequently poured into H2O (350 mL). The resulting suspension is extracted with EtOAc (1×500 mL) and the organic phase washed with 2M HCl (1×250 mL), H2O (5×500 mL), saturated NaCl solution (2×500 mL), dried over MgSO4 and concentrated in vacuo. The resulting material is triturated with hexanes, and recrystallized from EtOAc to give 2-[3-(4-fluorophenyl)-propyl]-6-[2-(N-aminocarbonyl-N-hydroxyamino)ethoxy]-1-oxo-1,2,3,4-tetrahydroisoquinoline, m.p. 138°-140°.

Workup

  1. extractionThe resulting suspension is extracted with EtOAc (1×500 mL)
  2. washthe organic phase washed with 2M HCl (1×250 mL), H2O (5×500 mL), saturated NaCl solution (2×500 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting material is triturated with hexanes
  6. customrecrystallized from EtOAc

Sources & evidence

ORD record
ord-ba34604eb15749a3a5b0194766127df3
Source dataset
uspto-grants-1994_09
Patent number
US05350761

Reaction notes

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