Sodium Hydroxide → 1-(4-carboxybutyl)-3-cyclohexyl-1H-indole-6-carboxylic acid

HRID 860728Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

2N NaOH solution (2.0 mL) was added to a solution of methyl 3-cyclohexyl-1-(5-methoxy-5-oxopentyl)-1H-indole-6-carboxylate (410 mg, 1.1 mmol) in THF/Methanol mixture (2.0 mL/2.0 mL). The reaction mixture was heated at 100° C. under microwave condition for 15 min, after which it was concentrated and the pH was adjusted to 4–5 with 1N HCl solution. A precipitate formed which was collected by filtration to give the product as a white powder, (375 mg, 99% yield). MS m/z 344(MH+). 1H NMR (300 MHz, CD3OD) δ ppm 1.24–1.98 (m, 10 H) 2.00–2.15 (m, 2 H) 2.25–2.39 (m,2H) 2.84 (m, 1 H) 4.16–4.30 (m, 2 H) 4.56–4.72 (m, 2 H) 7.22 (m, 1H) 7.58–7.78 (m, 2H) 8.10 (m, 1H).

Workup

concentrationafter which it was concentrated
customA precipitate formed which
filtrationwas collected by filtration

Sources & evidence

ORD record: ord-045e359dd0a245c9a6dbec77e867ba08
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153848B2

Reaction notes

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