Hydrochloric Acid → HCID 24884562, compound

HRID 1944503Notes

Reaction equation

HRID 1944503 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([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)[S:11][CH:12]=1.[Li+].[OH-].Cl.CCOC(C)=O>C1COCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([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)[S:11][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 59187439HCID 59187439, compound

Product 1

HCID 24884562HCID 24884562, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(4-((4-(2-bromophenyl)thiazol-2-yl)methoxy)-2-methylphenoxy)acetate (20 mg, 0.04 mmol) is dissolved in THF (1 mL). A solution of 1 M LiOH in H2O (0.2 mL) is added, and the mixture is stirred for 1 h at rt. The mixture is acidified with 1 M HCl (0.25 mL); EtOAc (10 mL) is added and the organic layer is washed with brine (5 mL). The organic layer is dried (MgSO4), filtered, concentrated and purified on reverse phase HPLC (H2O/MeCN gradient) to afford the title compound A1 as a white solid: 1H-NMR (400 MHz, CDCl3) δ=7.74 (dd, J=1.6, 8.0 Hz, 1H), 7.73 (s, 1H), 7.67 (dd, J=1.2, 8.0 Hz, 1H), 7.38 (dt, J=1.2, 7.6 Hz, 1H), 7.22 (dt, J=1.6, 7.6 Hz, 1H), 6.90 (d, J=2.8 Hz, 1H), 6.78 (dd, J=2.8, 8.8 Hz, 1H), 6.70 (d, J=8.8 Hz, 1H), 5.37 (s, 2H), 4.63 (s, 2H), 2.28 (s, 3H). MS calcd. for C19H17BrNO4S (M+H+) 434.0. found 433.9.

Workup

  1. washthe organic layer is washed with brine (5 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-5d81504e258042d3b83544ca2c5446e0
Source dataset
uspto-grants-2013_03
Patent number
US08394841B2

Reaction notes

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