Lithium Hydroxide → 3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(3-methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-propyl]-benzoic acid

HRID 2096904Notes

Reaction equation

HRID 2096904 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:28])[C:11]([OH:27])([C:16]2[CH:17]=[CH:18][C:19]3[O:23][C:22](=[O:24])[N:21]([CH3:25])[C:20]=3[CH:26]=2)[C:12]([F:15])([F:14])[F:13])=[C:6]([Cl:29])[CH:5]=1.[Li+].[OH-]>C1COCC1>[Cl:29][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[CH:10]([CH3:28])[C:11]([OH:27])([C:16]1[CH:17]=[CH:18][C:19]2[O:23][C:22](=[O:24])[N:21]([CH3:25])[C:20]=2[CH:26]=1)[C:12]([F:14])([F:13])[F:15])[C:3]([OH:30])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 666971033-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(3-methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-propyl]-benzoic acid methyl ester

Product 1

HCID 666971253-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(3-methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-propyl]-benzoic acidYield 46.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In analogy to Example 230, 3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(3-methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-propyl]-benzoic acid methyl ester (1.05 g) was saponified with LiOH solution (1M, 6.12 mL) in THF (15 mL) to give the title compound 3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(3-methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-propyl]-benzoic acid as an off-white foam (0.47 g). MS (m/e, ISP neg. ion)=428.3 [M−H+].

Sources & evidence

ORD record
ord-088b9f98adff4269a11ae94141b1c719
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

Loading…