Hydrochloric Acid → HCID 25017319, compound

HRID 1944509Notes

Reaction equation

HRID 1944509 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[S:12][C:11]([CH2:13][O:14][C:15]2[CH:26]=[CH:25][C:18]([O:19][CH2:20][C:21]([O:23]C)=[O:22])=[C:17]([CH3:27])[CH:16]=2)=[N:10][CH:9]=1.[Li+].[OH-].Cl>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[S:12][C:11]([CH2:13][O:14][C:15]2[CH:26]=[CH:25][C:18]([O:19][CH2:20][C:21]([OH:23])=[O:22])=[C:17]([CH3:27])[CH:16]=2)=[N:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59187436HCID 59187436, compound

Product 1

HCID 25017319HCID 25017319, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The solution of methyl 2-(4-((5-(2-chlorophenyl)thiazol-2-yl)methoxy)-2-methylphenoxy)acetate from Step A 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 (10 mL) and extracted with 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 E1 as a white solid: 1H-NMR (400 MHz, CDCl3) δ=7.96 (s, 1H), 7.50 (m, 2H), 7.30 (m, 2H), 6.89 (d, J=2.4 Hz, 1H), 6.77 (dd, J=2.4, 8.8 Hz, 1H), 6.71 (d, J=8.8 Hz, 1H), 5.33 (s, 2H), 4.64 (s, 2H), 2.29 (s, 3H). MS calcd. for C19H17ClNO4S (M+H+) 390.0. found 390.0.

Workup

  1. extractionextracted with 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-4489cded6cf24b71a9e2c9b7aa6a13d5
Source dataset
uspto-grants-2013_03
Patent number
US08394841B2

Reaction notes

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