Hydrochloric Acid → (4-{[4-(2-Chlorophenyl)-1,3-thiazol-2-yl]methoxy}-2-methylphenoxy)acetic acid

HRID 1944510Notes

Reaction equation

HRID 1944510 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[S:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[N:18]=2)=[CH:8][C:7]=1[CH3:26].[Li+].[OH-].Cl>O>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:17]1[N:18]=[C:14]([CH2:13][O:12][C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:27])=[O:2])=[C:7]([CH3:26])[CH:8]=2)[S:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59187442HCID 59187442, compound

Product 1

HCID 25017320(4-{[4-(2-Chlorophenyl)-1,3-thiazol-2-yl]methoxy}-2-methylphenoxy)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The solution of {4-[4-(2-chloro-phenyl)-thiazol-2-ylmethoxy]-2-methyl-phenoxy}-acetic acid methyl ester from Step C is treated with a solution of 1 M LiOH in H2O (1 mL), and the mixture is stirred for 12 h at rt. The mixture is acidified with 1 M HCl (1.2 mL) and extracted into EtOAc (20 mL). The organic layer is dried (MgSO4), filtered, concentrated and purified on reverse phase HPLC (H2O/MeCN gradient) to afford the title compound F1 as a white solid: MS calcd. for C19H17ClNO4S (M+H+) 390.0. found 390.0.

Workup

  1. extractionextracted into EtOAc (20 mL)
  2. dry with materialThe organic layer is dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on reverse phase HPLC (H2O/MeCN gradient)

Sources & evidence

ORD record
ord-43ba4c51956040ba969c3448f365cb29
Source dataset
uspto-grants-2013_03
Patent number
US08394841B2

Reaction notes

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