Lithium Hydroxide → 6-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-propyl]-phenoxy}-nicotinic acid

HRID 2386883Notes

Reaction equation

HRID 2386883 reaction equation
C[O:2][C:3](=[O:38])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:36])[C:18]([OH:35])([C:23]3[CH:24]=[CH:25][C:26]4[O:31][CH2:30][C:29](=[O:32])[N:28]([CH3:33])[C:27]=4[CH:34]=3)[C:19]([F:22])([F:21])[F:20])=[C:13]([Cl:37])[CH:12]=2)=[N:6][CH:5]=1.[Li+].[OH-]>>[Cl:37][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=1[CH:17]([CH3:36])[C:18]([OH:35])([C:23]1[CH:24]=[CH:25][C:26]2[O:31][CH2:30][C:29](=[O:32])[N:28]([CH3:33])[C:27]=2[CH:34]=1)[C:19]([F:20])([F:21])[F:22])[O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:38])=[O:2])=[CH:5][N:6]=1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 666972096-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-propyl]-phenoxy}-nicotinic acid methyl ester

Product 1

HCID 666971016-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-propyl]-phenoxy}-nicotinic acid

Procedure

In analogy to Example 228, 6-{3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-propyl]-phenoxy}-nicotinic acid methyl ester (Example 229) was hydrolyzed with 1 M aqueous LiOH solution (4 h, r.t.) to give the title compound as a white solid. MS (m/e, ISP neg. ion)=535.1 [M−H+].

Sources & evidence

ORD record
ord-17341e7bd8f64965b6ced3b1516ef33a
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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