Hydrochloric Acid → HCID 10049568, compound

HRID 2373493Notes

Reaction equation

C(O[CH2:5][C:6]1[N:7]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:31][CH:30]=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][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:10][CH:9]=2)(=O)C.[OH-].[K+].Cl>>[CH2:21]([O:20][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]([CH3:36])([CH3:38])[CH3:37])=[CH:33][CH:34]=1)[C:6]1[CH2:5][O:18][C:16](=[O:17])[C:15](=[O:19])[C:14]2=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14797Potassium Hydroxide

HCID 21964283HCID 21964283, compound

Product 1

HCID 10049568HCID 10049568, compound

Procedure

The title compound was prepared from [2-[(acetyloxy)methyl]-5-(benzyloxy)-1-(4-tert-butylbenzyl)-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 aqueous HCl, as described in step 7 of Example 1. The product was obtained as an off-white solid; mp: 233-234° C. Mass spectrum (ESI, [M+H]+) m/z 454. 1H NMR (400 MHz, DMSO-d6) δ 7.59-7.56 (m, 2H), 7.47 (d, 1H, J=7.33 Hz), 7.39 (t, 2H, J=7.33 Hz), 7.35-7.30 (m, 3H), 7.15 (d, 2H, J=8.40 Hz), 7.07 (dd, 1H, J=9.05 and 2.45 Hz), 5.87 (s, 2H), 5.42 (s, 2H), 5.16 (s, 2H), and 1.22 ppm (s, 9H).

Workup

customThe product was obtained as an off-white solid

Sources & evidence

ORD record: ord-6a8bb85dcfa7484fb39165959bf835e6
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459478B2

Reaction notes

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