Methanol → 6-(Decanoylamino)-1H-indole-4-carboxylic acid
Reaction equation
[C:1]([C:5]1[CH:13]=[C:12]([NH:14][C:15](=[O:25])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2)([O:3]C)=[O:2].[OH-].[K+].CO>O1CCCC1.O>[C:1]([C:5]1[CH:13]=[C:12]([NH:14][C:15](=[O:25])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2)([OH:3])=[O:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
Five hundred-fifteen mg of 4-carbomethoxy-6-(N-decanoylamino)indole [prepared by the method of Wender et al., PNAS, 83: 4214-4218 (1986)] was dissolved in 60 mL of tetrahydrofuran. This solution was treated with 3 mL of a 1N KOH solution in water and also with 5 mL of methanol. The mixture was heated at 80° C. for 32 h. During this period another 2.5 mL of 1N KOH was added in two portions. After cooling the mixture was concentrated in vacuo. The mixture was then diluted with water and acidified with concentrated hydrochloric acid. The mixture was then extracted with methylene chloride. The organic layers were dried over sodium sulfate and concentrated to afford 300 mg of 4-carboxy-6-(N-decanoylamino)indole (60% yield), mp 248°-50° C.
Workup
- temperatureAfter cooling the mixture
- concentrationwas concentrated in vacuo
- additionThe mixture was then diluted with water
- extractionThe mixture was then extracted with methylene chloride
- dry with materialThe organic layers were dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-be1a6dc2bea1497f913d90514311e300
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05750568
Reaction notes
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