Hydrochloric Acid → [2-bromo-6-(tert-butoxycarbonyl)-3-cyclohexyl-1H-indol-1-yl]acetic acid

HRID 1714006Notes

Reaction equation

[Br:1][C:2]1[N:3]([CH2:24][C:25]([O:27]C)=[O:26])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:5]=2.Cl>O>[Br:1][C:2]1[N:3]([CH2:24][C:25]([OH:27])=[O:26])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH:5]=2

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of LiOH monohydrate (4 eq) in H2O (0.05 M) was added to a solution of tert-butyl 2-bromo-3-cyclohexyl-1-(2-methoxy-2-oxoethyl)-1H-indole-6-carboxylate (1 eq) in a mixture THF: CH3OH (1:1) (from Step 6, 0.05 M). The reaction was heated at 50° C. for 2 h, before being allowed to cool to RT and reducing the volatiles in vacuo. The residue was then acidified with aqueous HCl (1 N) and the resultant precipitate filtered off, washed with water and dried in vacuo to afford the title compound (quant.); MS (ES+) m/z 436 (M+H)+, 438 (M+H)+.

Workup

temperatureto cool to RT
filtrationthe resultant precipitate filtered off
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-0f60e1b48e2b4854be2ab0042fd394c8
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795247B2

Reaction notes

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