Hydrochloric Acid → HCID 10380483, compound

HRID 2373491Notes

Reaction equation

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

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14797Potassium Hydroxide

HCID 21964284HCID 21964284, compound

Product 1

HCID 10380483HCID 10380483, compound

Procedure

The title compound was prepared from [2-[(acetyloxy)methyl]-5-(benzyloxy)-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 a yellow solid; mp: >291° C. (dec.). Mass spectrum (ESI, [M−H]−) m/z 306. 1H NMR (400 MHz, DMSO-d6) δ 12.37 (s, 1H), 7.54 (s, 1H), 7.49 (s, 1H), 7.48 (d, 2H, J=8.86 Hz), 7.39 (t, 2H, J=7.64 Hz), 7.32 (d, 1H, J=7.18 Hz), 7.04 (dd, 1H, J=8.71 and 2.59 Hz), 5.82 (s, 2H), and 5.16 ppm (s, 2H).

Workup

customThe product was obtained as a yellow solid

Sources & evidence

ORD record: ord-7e61729be21f4fac86924261fa01b3da
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459478B2

Reaction notes

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