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

HRID 410590Notes

Reaction equation

HRID 410590 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7](O)([CH3:9])[CH3:8])=[N:4][CH:3]=1.[SH:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15]>ClCCCl.O.[I-].[Zn+2].[I-]>[Br:1][C:2]1[S:6][C:5]([C:7]([S:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])([CH3:9])[CH3:8])=[N:4][CH:3]=1

Participants

6

Reactant 2

HCID 18050Methyl 3-mercaptopropionateHCID 227143062-(5-Bromo-1,3-thiazol-2-yl)propan-2-ol

Product 1

HCID 58456087Methyl 3-(2-(5-bromothiazol-2-yl)propan-2-ylthio)propanoateYield 96%

Reagents, catalysts & solvents 3

HCID 9883512zinc(II)iodideCatalystHCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

The product of Step 2 (9.00 g, 40.5 mmol) was taken up in 1,2-DCE (400 mL) before adding methyl 3-mercaptopropionate (9.74 g, 81 mmol) and zinc iodide (38.8 g, 122 mmol). The reaction was stirred at reflux for 5 h. The suspension was diluted with water and extracted with dichloromethane (2×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated. Flash chromatography (0-15% ethyl acetate in hexanes) provided methyl 3-{[2-(5-bromo-1,3-thiazol-2-yl)propan-2-yl]sulfanyl}propanoate (12.58 g, 96%) as a colorless oil. ESI: [M+H]+ m/z 323.9/326.0.

Workup

  1. temperatureat reflux for 5 h
  2. extractionextracted with dichloromethane (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-b7da0b5b0c3f461e8d096042eaff6c92
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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