Hydrogen Bromide → HCID 68494378, compound

HRID 1616590Notes

Reaction equation

HRID 1616590 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19]C)[N:12]=1.Br.[OH-].[Na+]>C(O)(=O)C>[OH:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:11]1[N:12]=[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:21])=[O:2])[S:9][CH:10]=1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 14798Sodium HydroxideHCID 59167790HCID 59167790, compound

Product 1

HCID 68494378HCID 68494378, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Dissolve 5-[4-(2-methoxy-phenyl)-thiazol-2-yl]-pentanoic acid methyl ester (3.20 g, 10.5 mmol) in acetic acid (50 mL, glacial), add HBr (50 mL, 48% aqueous solution) and heat to reflux under N2 for 6 hours. Add additional HBr (20 mL, 48% aqueous solution) and heat at reflux under N2 overnight. Adjust to pH 4 with 5N NaOH solution, extract with EtOAc (×2), dry over MgSO4 and concentrate to get 2.64 grams of a light brown solid. Recrystallize from EtOAc/hexanes to afford the title compound (2.14 g, 74%). MS (IS) 278 (M+1)+.

Workup

  1. temperatureheat
  2. temperatureto reflux under N2 for 6 hours
  3. temperatureheat
  4. temperatureat reflux under N2 overnight
  5. extractionextract with EtOAc (×2)
  6. dry with materialdry over MgSO4
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-873e228be98743bf853bce2c0a826d9e
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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