Trimethylsilyl isocyanate → HCID 9803758, compound

HRID 2226962Notes

Reaction equation

HRID 2226962 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:15]3[CH2:24][CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH2:26][CH2:27][NH:28][OH:29])[CH:21]=4)[C:16]3=[O:30])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C[Si]([N:35]=[C:36]=[O:37])(C)C>O1CCOCC1.C(Cl)Cl.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:15]3[CH2:24][CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH2:26][CH2:27][N:28]([C:36]([NH2:35])=[O:37])[OH:29])[CH:21]=4)[C:16]3=[O:30])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 18963909HCID 18963909, compound

Product 1

HCID 9803758HCID 9803758, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-(4'-fluoro-4-biphenylylmethyl)-6-[2-(N-hydroxyamino)ethoxy]-1-oxo-1,2,3,4-tetrahydroisoquinoline (~22.5 mmol) in 1,4-dioxane (50 ml) and methylene chloride (30 ml), is added trimethylsilylisocyanate (3.36 ml). The reaction mixture is stirred at room temperature overnight and is subsequently diluted with H2O (500 ml). The resulting solution is extracted with EtOAc (2×400 ml) and the combined EtOAc portions washed with 2N HCl (800 ml), saturated NaCl solution (800 ml), dried over MgSO4, and concentrated in vacuo. The resulting solid is recrystallized from EtOAc/hexanes to give 2-(4'-fluoro-4-biphenylylmethyl)-6-[2-(N-aminocarbonyl-N-hydroxyamino)-ethoxy]-1-oxo-1,2,3,4-tetrahydroisoquinoline, m.p. 171°-172°.

Workup

  1. extractionThe resulting solution is extracted with EtOAc (2×400 ml)
  2. washthe combined EtOAc portions washed with 2N HCl (800 ml), saturated NaCl solution (800 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting solid is recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-a290c8165cce4031b2e6691c54e5893c
Source dataset
uspto-grants-1994_09
Patent number
US05350761

Reaction notes

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