Methyl 3-mercaptopropionate → Methyl 3-((5-bromothiazol-2-yl)methylthio)propanoate

HRID 1040090Notes

Reaction equation

HRID 1040090 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH2:7]Br)=[N:4][CH:3]=1.[SH:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13].CCN(C(C)C)C(C)C>CN(C=O)C.O>[Br:1][C:2]1[S:6][C:5]([CH2:7][S:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 18050Methyl 3-mercaptopropionateHCID 81531DiisopropylethylamineHCID 594709305-Bromo-2-(bromomethyl)-1,3-thiazole

Product 1

HCID 67433835Methyl 3-((5-bromothiazol-2-yl)methylthio)propanoateYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-Bromo-2-(bromomethyl)-1,3-thiazole (1.34 g, 5.22 mmol) was dissolved in DMF (15 mL). Methyl 3-mercaptopropionate (0.689 g, 5.74 mmol) and DIEA (0.876 g, 6.78 mmol) were added, and the reaction was stirred at room temperature for 3 h. The reaction was diluted with water and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated. Flash chromatography (0-30% ethyl acetate in hexanes) afforded methyl 3-{[(5-bromo-1,3-thiazol-2-yl)methyl]sulfanyl}propanoate (1.45 g, 94%) as a pale yellow oil. MS BSI: [M+H]+ m/z 295.9/297.9.

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-435fb9ae1e034f3b843a9094a2b20d2b
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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