Phenacyl bromide → HCID 18628686, compound

HRID 1060738Notes

Reaction equation

HRID 1060738 reaction equation
[CH3:1][CH:2]([CH3:13])[CH2:3][CH:4]([C:10](=[S:12])[NH2:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O>C(O)C>[CH3:13][CH:2]([CH3:1])[CH2:3][CH:4]([C:10]1[S:12][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:11]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 18628765HCID 18628765, compound

Product 1

HCID 18628686HCID 18628686, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution comprised of ethyl 4-methyl-2-thiocarbamoylpentanoate (410 mg, 2 mmol) in ethanol (5 mL) was treated with 2-bromo-1-phenylethanone (400 mg, 2 mmol). The mixture was refluxed for 30 minutes and concentrated to provide ethyl 4-methyl-2-(4-phenylthiazol-2-yl)pentanoate as a crude product. The crude product was dissolved in methanol (5 mL, tech. grade) and the solution was treated with sodium hydroxide (100 mg, 2.5 mmol). The mixture was stirred for 2 hours and diluted with 0.1 M hydrochloric acid solution. The dilution was extracted with ethyl acetate (25 mL) and the extract was washed with water and brine, dried (MgSO4) and concentrated. Product was purified from the residue by flash column on silica gel (60° A) with 33% ethyl acetate in hexane to provide 4-methyl-2-(4-phenylthiazol-2-yl)pentanoic acid (500 mg, 1.8 mmol). Rf 0.33. 1H NMR (DMSO-d6): 0.96 (d, 6H), 1.71-1.79 (m, 3H), 3.61 (m, 1H), 7.12 (s, 1H), 7.32-7.41 (m, 5H). LCMS: 275.91 (M+H+).

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-aa6e4c9258e2433387995b7ec8035e62
Source dataset
uspto-grants-2003_02
Patent number
US06525036B2

Reaction notes

Loading…