Sodium Hydroxide → HCID 18368053, compound

HRID 379887Notes

Reaction equation

HRID 379887 reaction equation
[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[N:7](C(OCC)=O)[C:6]=1[C:20]([C:22]1[O:23][CH:24]=[CH:25][C:26]=1[CH2:27][O:28]C(=O)C)=[O:21])(=[O:3])[CH3:2].[OH-].[Na+].[Cl-].[NH4+]>C(O)C.O>[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:20]([C:22]1[O:23][CH:24]=[CH:25][C:26]=1[CH2:27][OH:28])=[O:21])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 18367894HCID 18367894, compound

Product 1

HCID 18368053HCID 18368053, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-acetylamino-6-chloro-1-ethoxycarbonyl-2-(3-acetoxymethyl-2-furoyl) indole (step 3, 180 mg, 0.4 mmol) in a mixture of ethanol (10 ml) and water (5 ml) was added 2N aqueous sodium hydroxide (2 ml) at room temperture. After stirring for 1.5 h, the mixture was poured into saturated aqueous ammonium chloride (50 ml) and extracted with ethyl acetate (100 ml). The organic layer was washed with brine (50 ml), dried (MgSO4) and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate/hexane (1/1), and the product recrystalized from acetone/hexane to give 98 mg (73%) of the titled compound as a yellow crystalline solid. m.p.: 196-198° C. 1H-NMR (CDCl3) δ: 10.6 (1H, br s), 9.52 (1H, br s), 8.33 (1H, d, J=9.2 Hz), 7.66 (1H, br s), 7.30 (1H,br s), 7.01 (1H, d, J=9.2 Hz), 6.66 (1H, br s), 4.81 (2H, s), 2.32 (3H, s). The signal due to H of OH was not observed.

Workup

  1. extractionextracted with ethyl acetate (100 ml)
  2. washThe organic layer was washed with brine (50 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography
  6. washeluting with ethyl acetate/hexane (1/1)
  7. customthe product recrystalized from acetone/hexane

Sources & evidence

ORD record
ord-545443d1b72540f0b846e786cd8b4f59
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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