Tetrahydrofuran → HCID 68493107, compound

HRID 1616607Notes

Reaction equation

HRID 1616607 reaction equation
C[O:2][C:3](=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:19][C:20](=[O:22])[CH3:21])[N:12]=1.C1COCC1.[OH-].[Na+]>CCO>[C:20]([NH: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:23])=[O:2])[O:9][CH:10]=1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59167781HCID 59167781, compound

Product 1

HCID 68493107HCID 68493107, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 5-[4-(2-acetylamino-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester (3.26 g, 10.3 mmol) with THF (3 mL), EtOH (3 mL) and 1 N NaOH (40 mL) and stir at room temperature until hydrolysis is complete. Concentrate the mixture and dilute the residue with water before adjusting to pH 3.5-4.0 with aq HCl. Extract the mixture with 1-2% MeOH/EtOAc and concentrate the combined extracts in vacuo. Chromatograph the resulting residue over silica gel (MeOH/CH2Cl2) which allows for isolation of 5-[4-(2-acetylamino-phenyl)-oxazol-2-yl]-pentanoic acid (2.76 g, 89%). MS (ES): (M−1)− 301.2, 302.3.

Workup

  1. concentrationConcentrate the mixture
  2. additiondilute the residue with water
  3. extractionExtract the mixture with 1-2% MeOH/EtOAc
  4. concentrationconcentrate the combined extracts in vacuo

Sources & evidence

ORD record
ord-767fca9bd6cb49ba93b806ccb80b33e1
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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