Sodium Hydroxide → HCID 18368062, compound

HRID 379892Notes

Reaction equation

HRID 379892 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[C:8]([C:11]([C:13]2[N:14](C(OCC)=O)[C:15]3[C:20]([C:21]=2[NH:22][C:23](=[O:26])[CH2:24][CH3:25])=[CH:19][CH:18]=[C:17]([Cl:27])[CH:16]=3)=[O:12])[O:9][CH:10]=1)(=O)C.[OH-].[Na+].[Cl-].[NH4+]>C(O)C>[Cl:27][C:17]1[CH:16]=[C:15]2[C:20]([C:21]([NH:22][C:23](=[O:26])[CH2:24][CH3:25])=[C:13]([C:11]([C:8]3[O:9][CH:10]=[C:6]([CH2:5][OH:4])[CH:7]=3)=[O:12])[NH:14]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 183677572-(4-Acetoxymethyl-2-furoyl)-6-chloro-1-ethoxycarbonyl-3-(propionylamino)indole

Product 1

HCID 18368062HCID 18368062, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(4-acetoxymethyl-2-furoyl)-6-chloro-1-ethoxycarbonyl-3-(propionylamino)indole (step 1, 114 mg, 0.313 mmol) in ethanol (2 ml) was added 2N aqueous sodium hydroxide (2 ml). After stirring for 3 h, the mixture was poured into saturated aqueous ammonium chloride (20 ml) and extracted with ethyl acetate (80 ml). The organic layer was washed with brine (20 ml), dried (MgSO4) and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate/hexane (1/1) and recrystalization from 2-propanol/isopropyl ether to give 46 mg (40%) of the titled compound as yellow solids. m.p.: 171-172° C. 1H-NMR (CDCl3) δ: 10.74 (1H, br s), 9.37 (1H, br s), 8.45 (1H, d, J=9.06 Hz), 7.08 (1H, s), 7.42 (1H, s), 7.36 (1H, d, J=1.81 Hz), 7.06 (1H, dd, J=9.06 Hz, 1.81 Hz), 4.67 (2H, s), 2.58 (2H, q, J=7.58 Hz), 1.33 (3H, t, J=7.58 Hz).

Workup

  1. extractionextracted with ethyl acetate (80 ml)
  2. washThe organic layer was washed with brine (20 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) and recrystalization from 2-propanol/isopropyl ether

Sources & evidence

ORD record
ord-f758586dd0864e0caf5e440e6d42919d
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

Loading…