1-(tert-Butyloxycarbonyl-methyl)-1H-indole-2-carboxylic acid ethyl ester → 1-(carboxy-methyl)-1H-indole-2-carboxylic ethyl ester
Reaction equation
C([O:5][C:6](=[O:22])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])(C)(C)C>C(O)=O>[CH2:20]([O:19][C:17]([C:9]1[N:8]([CH2:7][C:6]([OH:22])=[O:5])[C:16]2[C:11]([CH:10]=1)=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:18])[CH3:21]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A solution of ethyl 1-(2-tert-butoxy-2-oxoethyl)-1H-indole-2-carboxylate (4.64 g) is 25 mL of formic acid (88%) was heated at 100° C. for 1 hr. TLC showed that the reaction was complete. The solvent was removed by evaporation and the residue was triturated with water and filtered to collect the solid. The beige solid was air dried overnight to afford 3.78 g of the desired product.
Workup
- customThe solvent was removed by evaporation
- customthe residue was triturated with water
- filtrationfiltered
- customto collect the solid
- customdried overnight
Sources & evidence
- ORD record
- ord-76191fde256044589ba1e952ced39864
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09345905B2
Reaction notes
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