Hydrochloric Acid → HCID 10001646, compound

HRID 2373490Notes

Reaction equation

HRID 2373490 reaction equation
[C:1]([O:4][CH2:5][C:6]1[N:7]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)[C:8]2[C:13]([C:14]=1[C:15](=[O:19])C(O)=O)=[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:3])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]([CH3:35])=[CH:33][CH:34]=1)[C:6]1[CH2:5][O:4][C:1](=[O:3])[C:15](=[O:19])[C:14]2=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 21964285HCID 21964285, compound

Product 1

HCID 10001646HCID 10001646, compound

Procedure

The title compound was prepared from [2-[(acetyloxy)methyl]-5-(benzyloxy)-1-(4-methylbenzyl)-1H-indol-3-yl](oxo)acetic acid and aqueous potassium hydroxide according to the procedure described in step 6 of Example 1, followed by the treatment with aqueous HCl in substantially the same manner, as described in step 7 of Example 1. The product was obtained as an off-white solid; mp: 206-207° C. Mass spectrum (ESI, [M+H]+) m/z 412. 1H NMR (400 MHz, DMSO-d6) δ 7.58 (s, 1H), 7.54 (d, 1H, J=9.01 Hz), 7.47 (d, 2H, J=7.33 Hz), 7.38 (t, 2H, J=8.63 Hz), 7.31 (t, 1H, J=7.18 Hz), 7.15-7.11 (m, 4H,), 7.05 (dd, 2H, J=9.44 and 2.44 Hz), 5.86 (s, 2H), 5.41 (s, 2H), 5.16 (s, 2H), 2.25 ppm (s, 3H).

Workup

  1. customThe product was obtained as an off-white solid

Sources & evidence

ORD record
ord-11ee78f754984685990c22edff229c55
Source dataset
uspto-grants-2008_12
Patent number
US07459478B2

Reaction notes

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