Sodium Hydroxide → HCID 86641005, compound

HRID 422876Notes

Reaction equation

HRID 422876 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]2([CH2:19][O:18][C:17]3[CH:20]=[C:21]4[C:25](=[CH:26][C:16]2=3)[C:24](=O)[CH2:23][O:22]4)[C:8]1=[O:28].Cl.[NH2:30][OH:31].C([O-])(=O)C.[Na+].[OH-].[Na+]>CO.O1CCCC1>[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]2([CH2:19][O:18][C:17]3[CH:20]=[C:21]4[C:25](=[CH:26][C:16]2=3)[C:24](=[N:30][OH:31])[CH2:23][O:22]4)[C:8]1=[O:28]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 46195567HCID 46195567, compound

Product 1

HCID 86641005HCID 86641005, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1′-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indole]-2′,5(1′H,6H)-dione (0.25 g, 0.66 mmol) in methanol (10 mL) and tetrahydrofuran (10 mL) were added hydroxylamine hydrochloride (0.92 g, 13.3 mmol) and sodium acetate (1.09 g, 13.3 mmol). The reaction mixture was stirred for 48 h at ambient temperature. To the reaction mixture was added 1 N sodium hydroxide to adjust pH>9. The mixture was extracted with ethyl acetate (2×50 mL). The combined organic solution was washed with water and brine, then dried over sodium sulfate, filtered and concentrated to afford 1′-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indole]-2′,5(1′H,6H)-dione 5-oxime (0.25 g, 96%) as a colorless solid: mp 82-100° C.; 1H NMR (300 MHz, CDCl3) δ 8.00-7.50 (br, 1H), 7.49-6.83 (m, 5H), 6.52-6.46 (m, 1H), 5.10-4.93 (m, 3H), 4.76-4.69 (m, 1H), 4.30-5.19 (m, 1H), 3.95-3.66 (m, 4H), 2.08-1.60 (m, 4H); MS (ES+) m/z 392.9 (M+1), 414.9 (M+23).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
  2. washThe combined organic solution was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-12a5581fcf9e47f49a3e6bd62d06dc2a
Source dataset
uspto-grants-2012_01
Patent number
US08101647B2

Reaction notes

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