Pyridine → HCID 59167783, compound

HRID 1616604Notes

Reaction equation

HRID 1616604 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-9c19e257f448436197d07c9be94ea3fd
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

Loading…