Sodium Hydroxide → HCID 21864963, compound

HRID 856956Notes

Reaction equation

HRID 856956 reaction equation
[C:1]([N:4]([C:8]1[C:9]2[CH:30]=[C:29]3[C:24]([CH2:25][CH2:26][CH2:27][CH2:28]3)=[CH:23][C:10]=2[O:11][C:12]=1[C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])C(=O)C)(=[O:3])[CH3:2].[OH-].[Na+].C(OCC)(=O)C.CCCCCC>C1COCC1.C(OCC)(=O)C>[Cl:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[C:13]([C:12]1[O:11][C:10]2[CH:23]=[C:24]3[C:29](=[CH:30][C:9]=2[C:8]=1[NH:4][C:1](=[O:3])[CH3:2])[CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:22]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21226206Ethyl acetate hexaneHCID 21864953HCID 21864953, compound

Product 1

HCID 21864963HCID 21864963, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-acetyl-N-[2-(2,4-dichlorobenzoyl)-5,6,7,8-tetrahydronaphtho[2,3-b]furan-3-yl]-acetamide (40 mg, 0.09 mmol) in anhydrous THF (1.8 mL) was added 2N sodium hydroxide solution (1.8 mL), and the reaction mixture was stirred at 100° C. for 1 h. The reaction was diluted with ethyl acetate, washed with saturated aqueous ammonium chloride solution, water, and brine. The organic layer was then dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude product was purified on the MPLC (Biotage) eluted with 5% ethyl acetate-hexane to afford 24.5 mg (67.6%) as yellow foam. 1H-NMR (DMSO-d6) δ 10.22 (s, 1H), 7.79 (t, J=1.2 Hz, 1H), 7.62 (s, 1H), 7.58 (d, J=0.9 Hz, 2H), 7.30 (s, 1H), 2.84 to 2.79 (m, 4H), 2.06 (s, 3H), 1.74 to 1.72 (m, 4H); LC-MS (ES MH+=402); Rf=0.68 (25% ethyl acetate-hexane).

Workup

  1. washwashed with saturated aqueous ammonium chloride solution, water, and brine
  2. dry with materialThe organic layer was then dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe crude product was purified on the MPLC (Biotage)
  6. washeluted with 5% ethyl acetate-hexane
  7. customto afford 24.5 mg (67.6%) as yellow foam

Sources & evidence

ORD record
ord-e6a8f225bb64471a97ea25568c79d32c
Source dataset
uspto-grants-2006_12
Patent number
US07144885B2

Reaction notes

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