Sodium Hydroxide → HCID 18368213, compound

HRID 379890Notes

Reaction equation

HRID 379890 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:28])[CH2:24][CH:25]([CH3:27])[CH3:26])=[CH:19][CH:18]=[C:17]([Cl:29])[CH:16]=3)=[O:12])[O:9][CH:10]=1)(=O)C.[OH-].[Na+].[Cl-].[NH4+]>C(O)C>[Cl:29][C:17]1[CH:16]=[C:15]2[C:20]([C:21]([NH:22][C:23](=[O:28])[CH2:24][CH:25]([CH3:26])[CH3:27])=[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 183679002-(4-Acetoxymethyl-2-furoyl)-6-chloro-1-ethoxycarbonyl-3-(isovalerylamino)indole

Product 1

HCID 18368213HCID 18368213, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(4-acetoxymethyl-2-furoyl)-6-chloro-1-ethoxycarbonyl-3-(isovalerylamino)indole (step 3, 213.5 mg, 0.437 mmol) in ethanol (1.5 ml) was added 2N aqueous sodium hydroxide (1.5 ml). After stirring for 5.5 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 cocentrated. The residue was purified by flash column chromatography eluting with ethyl acetate/hexane (1/3) and recrystallization from 2-propanol/isopropyl ether to give 119 mg (88%) of the titled compound as yellow solids. m.p: 200-201° C.

Workup

  1. extractionextracted with ethyl acetate (80 ml)
  2. washThe organic layer was washed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. customThe residue was purified by flash column chromatography
  5. washeluting with ethyl acetate/hexane (1/3) and recrystallization from 2-propanol/isopropyl ether

Sources & evidence

ORD record
ord-70aa23161f91460b94cad6c0d3871b5b
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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