Hydrochloric Acid → HCID 21964307, compound

HRID 2373497Notes

Reaction equation

C(O[CH2:5][C:6]1[N:7]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=2)[C:8]2[C:13]([C:14]=1[C:15](=[O:19])[C:16]([OH:18])=[O:17])=[CH:12][C:11]([O:20][CH3:21])=[CH:10][CH:9]=2)(=O)C.[OH-].[K+].Cl>>[C:29]([C:26]1[CH:27]=[CH:28][C:23]([CH2:22][N:7]2[C:8]3[C:13](=[CH:12][C:11]([O:20][CH3:21])=[CH:10][CH:9]=3)[C:14]3[C:15](=[O:19])[C:16](=[O:17])[O:18][CH2:5][C:6]2=3)=[CH:24][CH:25]=1)([CH3:31])([CH3:32])[CH3:30]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14797Potassium Hydroxide

HCID 21964297HCID 21964297, compound

Product 1

HCID 21964307HCID 21964307, compound

Procedure

The title compound was prepared from [2-[(acetyloxy)methyl]-1-(4-tert-butylbenzyl)-5-methoxy-1H-indol-3-yl](oxo)acetic acid and aqueous potassium hydroxide in substantially the same manner as described in step 6 of Example 1, followed by the treatment with aq HCl in substantially the same manner as described in step 7 of Example 1. The product was obtained as an off-white solid; mp: 238-239° C. Mass spectrum (ESI, [M−H]−) m/z 376. 1H NMR (400 MHz, DMSO-d6) δ 7.56 (d, 1H, J=9.01 Hz), 7.48 (d, 1H, J=2.45 Hz), 7.35 (d, 2H, J=8.40 Hz), 7.14 (d, 2H, J=8.25 Hz), 6.98 (dd, 1H, J=8.86 and 2.44 Hz), 5.87 (s, 2H), 5.42 (s, 2H), 3.81 (s, 3H), 1.22 ppm (s, 9H).

Workup

customThe product was obtained as an off-white solid

Sources & evidence

ORD record: ord-4351f52f4ec348e8bc2075c198e5f097
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459478B2

Reaction notes

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