HCID 68489904, compound → 5-[5-(2-Methoxy-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester

HRID 1039194Notes

Reaction equation

HRID 1039194 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:21])[NH:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])=O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:21][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])=[CH:10][N:9]=1

Participants

4

Reactant 1

HCID 68489904HCID 68489904, compound

Product 1

HCID 591677925-[5-(2-Methoxy-phenyl)-oxazol-2-yl]-pentanoic acid methyl esterYield 57.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Dissolve 5-[2-(2-methoxy-phenyl)-2-oxo-ethylcarbamoyl]-pentanoic acid methyl ester (4.57 g, 14.87 mmol) and 4-(dimethylamino)pryidine (3.56 g, 29.14 mmol) in 150 mL CH2Cl2 and cool the reaction mixture in an ice bath. Add triphenylphosphinedibromide (12.32 g, 1.96 mmol) to the reaction portionwise over 15 minutes. Raise the reaction to ambient temperature and allow it to stir for 12 hours. Wash the reaction with water and brine (2×). Dry the organic layers with MgSO4. Filter off the drying agent and concentrate in vacuo to afford a crude residue. Purify the residue using silica gel chromatography eluting with hexanes/ethyl acetate mixtures to afford 2.47 g of the titled product (57%): mass spectrum: m/z=290.1 (M+H).

Workup

  1. temperaturecool the reaction mixture in an ice bath
  2. additionAdd triphenylphosphinedibromide (12.32 g, 1.96 mmol)
  3. customto the reaction portionwise over 15 minutes
  4. temperatureRaise
  5. customthe reaction to ambient temperature
  6. washWash
  7. customthe reaction with water and brine (2×)
  8. dry with materialDry the organic layers with MgSO4
  9. filtrationFilter off the drying agent
  10. concentrationconcentrate in vacuo
  11. customto afford a crude residue
  12. customPurify the residue
  13. washeluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-7c945ebb7c314a6888180a0c819295d6
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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