Tetrahydrofuran → HCID 68490626, compound

HRID 1039219Notes

Reaction equation

HRID 1039219 reaction equation
C[O:2][C:3](=[O:24])[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][S:20]([CH3:23])(=[O:22])=[O:21])[N:12]=1.C1COCC1.[OH-].[Na+]>CCO>[CH3:23][S: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:24])=[O:2])[O:9][CH:10]=1)(=[O:21])=[O:22]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59167783HCID 59167783, compound

Product 1

HCID 68490626HCID 68490626, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 5-[4-(2-methanesulfonylamino-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester (2.75 g, 7.8 mmol) with THF (3 mL), EtOH (3 mL) and 1N NaOH (20 mL) and stir at room temperature until hydrolysis is complete. Concentrate the mixture and dilute the residue with water and adjust to pH 3.0-3.5 with aq HCl. Extract the mixture with EtOAc and dry the extracts over Na2SO4 before concentrating. Chromatograph the residue over silica gel (EtOAc) to allow for recovery of 5-[4-(2-methanesulfonylamino-phenyl)-oxazol-2-yl]-pentanoic acid (2.16 g, 82%). MS (ES): (M+1)+ 339.2, 340.3.

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-663cdfa2414641ef886727c17024b01c
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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