Methyl 6-bromo-5-oxohexanoate → Methyl 4-(2-amino-1,3-thiazol-4-yl)butanoate

HRID 618134Notes

Reaction equation

HRID 618134 reaction equation
Br[CH2:2][C:3](=O)[CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].[NH2:12][C:13]([NH2:15])=[S:14]>CCO>[NH2:15][C:13]1[S:14][CH:2]=[C:3]([CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])[N:12]=1

Participants

4

Reactant 2

HCID 582216Methyl 6-bromo-5-oxohexanoateHCID 2723790Thiourea

Product 1

HCID 21699734Methyl 4-(2-amino-1,3-thiazol-4-yl)butanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Bromide 1-2 (3.45 g, 15.5 mmol) and thiourea (1.4 g, 18 mmol) were combined in 77 mL EtOH and heated to reflux. After disappearance of 1-2, the EtOH was removed by rotary evaporation and the residue was diluted with EtOAc, washed with water and brine, then dried (MgSO4), filtered and concentrated. The pH of the aqueous phase was adjusted to 7, and the solution was re-extracted with EtOAc (2×). These organic extracts were washed with brine, dried (MgSO4), filtered and concentrated, combined with the first organic residues, then purified by flash chromatography (silica, EtOAc) providing aminothiazole 1-3 as a white solid.

Workup

  1. temperatureheated to reflux
  2. customAfter disappearance of 1-2, the EtOH was removed by rotary evaporation
  3. additionthe residue was diluted with EtOAc
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. extractionthe solution was re-extracted with EtOAc (2×)
  9. washThese organic extracts were washed with brine
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. custompurified by flash chromatography (silica, EtOAc)

Sources & evidence

ORD record
ord-dc5f445633674670be2729c6bd3ceff5
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

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