Tetrahydrofuran → HCID 136400605, compound

HRID 1616636Notes

Reaction equation

HRID 1616636 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[N:9]=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[S:11][CH:12]=1.C1COCC1.[OH-].[Na+]>CCO>[OH:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:10]1[S:11][CH:12]=[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:20])=[O:2])[N:9]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 136400604HCID 136400604, compound

Product 1

HCID 136400605HCID 136400605, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 5-[2-(2-hydroxy-phenyl)-thiazol-4-yl]-pentanoic acid methyl ester (2.2 g, 7.6 mmol) with THF (2.5 mL), EtOH (2.5 mL) and 2N NaOH (14 mL) and stir until hydrolysis is complete. Concentrate the mixture, dilute the residue with water and adjust the pH to 2.0-3.0 using aqueous HCl. Extract the mixture with EtOAc and dry the extracts over Na2SO4 before concentrating. Chromatograph the residue over silica gel (MeOH/CH2Cl2) to allow for recovery of 5-[2-(2-hydroxy-phenyl)-thiazol-4-yl]-pentanoic acid (1.5 g, 72%). MS (ES): (M+1)+ 278.1 m/z.

Workup

  1. concentrationConcentrate the mixture
  2. additiondilute the residue with water
  3. extractionExtract the mixture with EtOAc
  4. dry with materialdry the extracts over Na2SO4
  5. concentrationbefore concentrating

Sources & evidence

ORD record
ord-580dffb1c8444c71ade75355de1ec530
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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