Potassium Hydroxide → N-(5-carboxypentyl)-3-(1-naphthoyl)-1H-indole

HRID 55923

Reaction equation

C([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)=[O:21])=[CH:12]1)=[O:5])C.[OH-].[K+]>C1COCC1.O>[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)=[O:21])=[CH:12]1)([OH:5])=[O:3]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2 (5.0 g, 12 mmol) in a mixture of THF/H2O (1:1) was added potassium hydroxide (1.7 g) and the mixture was stirred at 60° C. for 1 h. The THF was removed under vacuum, the aqueous solution acidified to pH 1 by the addition of hydrochloric acid solution (1N) and extracted by ethyl acetate (3×100 ml). The combined organic phases were washed by water (100 ml), brine solution (100 ml), dried over sodium sulphate, filtered and concentrated to dryness. The crude product obtained was dissolved in ethyl acetate (10 ml) and the Hapten-A precipitated by the addition of a mixture of ether/hexane as a white solid, filtered and dried under high vacuum to give Hapten-A (3.6 g, 78%).

Workup

customThe THF was removed under vacuum
additionthe aqueous solution acidified to pH 1 by the addition of hydrochloric acid solution (1N)
extractionextracted by ethyl acetate (3×100 ml)
washThe combined organic phases were washed by water (100 ml), brine solution (100 ml)
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-17e8838374e3476c959697b133c82e3a
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434687B2

Linked notes

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