Sodium Hydroxide → (2S)-2-Methoxy-3-(4-{3-[4-(2,2,3,3-tetrafluoro-propoxy)-phenoxy]-propoxy}-phenyl)-propionic acid

HRID 459283Notes

Reaction equation

C([O:3][C:4](=[O:34])[C@@H:5]([O:32][CH3:33])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]([F:31])([F:30])[CH:27]([F:29])[F:28])=[CH:20][CH:19]=2)=[CH:9][CH:8]=1)C.[OH-].[Na+]>>[CH3:33][O:32][C@@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][C:26]([F:30])([F:31])[CH:27]([F:29])[F:28])=[CH:22][CH:23]=2)=[CH:11][CH:12]=1)[C:4]([OH:34])=[O:3]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 58822582(2S)-2-Methoxy-3-(4-{3-[4-(2,2,3,3-tetrafluoro-propoxy)-phenoxy]-propoxy}-phenyl)-propionic acid ethyl ester

Product 1

HCID 58822741(2S)-2-Methoxy-3-(4-{3-[4-(2,2,3,3-tetrafluoro-propoxy)-phenoxy]-propoxy}-phenyl)-propionic acid

Procedure

The title compound was prepared from (2S)-2-methoxy-3-(4-{3-[4-(2,2,3,3-tetrafluoro-propoxy)-phenoxy]-propoxy}-phenyl)-propionic acid ethyl ester (Step C) by standard hydrolysis procedure C (NaOH). 1H-NMR (CDCl3, 200.15 MHz): δ 7.14 (d, 2H, J=8.6), 6.84–6.79 (m, 6H), 6.04 (tt, 1H, J=53.0, 4.8), 4.27 (t, 2H, J=12.0), 4.09 (t, 4H, J=5.9), 3.97–3.91 (m, 1H), 3.34 (s, 3H), 3.11–2.87 (m, 2H), 2.20 (qn, 2H, J=5.9).

Sources & evidence

ORD record: ord-67a749760fdd4950b8bfb61c73d5692f
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192982B2

Reaction notes

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