Tetrahydrofuran → 4-[4-(2-Amino-phenyl)-oxazol-2-yl]-butyric acid

HRID 1039237Notes

Reaction equation

HRID 1039237 reaction equation
C[O:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][C:7]1[O:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])[N:11]=1.C1COCC1.[OH-].[Na+]>CCO>[NH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:10]1[N:11]=[C:7]([CH2:6][CH2:5][CH2:4][C:3]([OH:19])=[O:2])[O:8][CH:9]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 591677464-[4-(2-Amino-phenyl)-oxazol-2-yl]-butyric acid methyl ester

Product 1

HCID 597990014-[4-(2-Amino-phenyl)-oxazol-2-yl]-butyric acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 4-[4-(2-amino-phenyl)-oxazol-2-yl]-butyric acid methyl ester (2.36 g, 9.1 mmol) with THF (3 mL), EtOH (3 mL) and 2N NaOH (20 mL) and stir until hydrolysis is complete. Concentrate the mixture, dilute the residue with water and adjust the pH to 3.5-4.0 with aq 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 4-[4-(2-amino-phenyl)-oxazol-2-yl]-butyric acid (1.63 g, 73%). MS (ES): (M+1)+ 247.1 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-ed271b4048e54a86835edd1a02626501
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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