Water → 4-(tert-butoxycarbonyl)-1H-indole-7-carboxylic acid

HRID 906115Notes

Reaction equation

[NH:1]1[C:9]2[C:8]([C:10]([O:12]C)=[O:11])=[CH:7][CH:6]=[C:5]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:4]=2[CH:3]=[CH:2]1.O1CCCC1.O.[OH-].[Li+]>CO>[C:17]([O:16][C:14]([C:5]1[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[C:9]2[C:4]=1[CH:3]=[CH:2][NH:1]2)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 4-tert-butyl 7-methyl 1H-indole-4,7-dicarboxylate (0.58 g, 2.10 mmol) in a mixture of methanol (20 mL), terahydrofuran (10 mL) and water (10 mL) was added a 2M aqueous solution of lithium hydroxide (2.1 mL, 4.20 mmol), and the reaction mixture was stirred at 40° C. until full consumption of starting material. The organic portion of the solvent was evaporated and the pH of the aqueous solution was adjusted to 3-4 by the addition of 1 M aqueous hydrochloric acid. The acidic aqueous phase was partitioned with ethyl acetate (150 mL), and the organic layer was separated and washed with brine, dried over sodium sulfate, filtered and concentrated to give 4-(tert-butoxycarbonyl)-1H-indole-7-carboxylic acid (0.36 g, 67%). MS (EI) for C14H15NO4: 260 (M−H).

Workup

customThe organic portion of the solvent was evaporated
additionthe pH of the aqueous solution was adjusted to 3-4 by the addition of 1 M aqueous hydrochloric acid
customThe acidic aqueous phase was partitioned with ethyl acetate (150 mL)
customthe organic layer was separated
washwashed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-d7d6b15f56a443b0917ed75157ae86a5
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012956B2

Reaction notes

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