Pyridine → HCID 59167783, compound

HRID 1039218Notes

Reaction equation

HRID 1039218 reaction equation
[CH3:1][O:2][C:3](=[O:20])[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[NH2:19])[N:12]=1.N1C=CC=CC=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C1COCC1>[CH3:1][O:2][C:3](=[O:20])[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:28]([CH3:27])(=[O:30])=[O:29])[N:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 59167769HCID 59167769, compound

Product 1

HCID 59167783HCID 59167783, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 5-[4-(2-amino-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester (2.18 g, 7.96 mmol) in THF (50 mL) and add pyridine (1.20 mL, 14.8 mmol). Add methanesulfonyl chloride (excess) and allow the mixture to stir at room temperature until reaction is complete. Concentrate the mixture and quench the residue with ice/aq NaHCO3 and extract with EtOAc. Dry the combined extracts over Na2SO4 and concentrate. Chromatograph the residue over silica gel (EtOAc/CH2Cl2) to allow for isolation of 5-[4-(2-methanesulfonylamino-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester (2.8 g, 100%). MS (ES): (M+1)+ 353.2, 354.3 m/z.

Workup

  1. concentrationConcentrate the mixture
  2. customquench the residue with ice/aq NaHCO3
  3. extractionextract with EtOAc
  4. dry with materialDry the combined extracts over Na2SO4
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-5809ca5ac19d47799bc658300da48732
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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