Lithium Hydroxide → 5-(1-Carboxy-1-methyl-ethoxy)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

HRID 966500Notes

Reaction equation

HRID 966500 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][C:21]([C:24]([O:26]CC)=[O:25])([CH3:23])[CH3:22])[CH:18]=2)[NH:13][C:12]=1[CH3:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.O.C(OC(=O)C)C.CCCCCC>[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][C:21]([C:24]([OH:26])=[O:25])([CH3:23])[CH3:22])[CH:18]=2)[NH:13][C:12]=1[CH3:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 233938615-(1-Ethoxycarbonyl-1-methyl-ethoxy)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

Product 1

HCID 233938135-(1-Carboxy-1-methyl-ethoxy)-2-methyl-1H-indole-3-carboxylic Acid Benzyl EsterYield 84%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

5-(1-Ethoxycarbonyl-1-methyl-ethoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (6.88 g, 16.5 mmol, 1.0 eq) was dissolved in THF (16 mL), followed by LiOH (0.395 g, 16.5 mmol, 1.0 eq) in H2O (16 mL). The reaction mixture was refluxed for 24 hours. Another equivalent of LiOH was added, and reflux was continued for another 24 hours. The reaction was then judged complete by TLC in hexane ethyl acetate 1:1. 5.0 g of the product was obtained, 84% yield (crude).

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hours
  2. temperaturereflux

Sources & evidence

ORD record
ord-705ea77ea7b645d7a5b9db18553dd5bf
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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