Methanol → Methyl 3-{[2-(5-bromo-1,3-thiazol-2-yl)propan-2-yl]sulfonyl}propanoate

HRID 410591Notes

Reaction equation

HRID 410591 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([S:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])([CH3:9])[CH3:8])=[N:4][CH:3]=1.CO.[OH2:19].[OH2:20].O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=O.[Mg+2]>ClCCl.[O-]S([O-])(=S)=O.[Na+].[Na+].O>[Br:1][C:2]1[S:6][C:5]([C:7]([S:10]([CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])(=[O:20])=[O:19])([CH3:9])[CH3:8])=[N:4][CH:3]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)HCID 58456087Methyl 3-(2-(5-bromothiazol-2-yl)propan-2-ylthio)propanoate

Product 1

HCID 67258095Methyl 3-{[2-(5-bromo-1,3-thiazol-2-yl)propan-2-yl]sulfonyl}propanoateYield 96%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

The product of Step 3 (12.50 g, 38.5 mmol) was taken up in dichloromethane (250 mL)/methanol (125 mL), and magnesium monoperoxyphthalate hexahydrate (35.8 g, 57.8 mmol) was added. The reaction was stirred at room temperature for 2 h. The white slurry was diluted with 10% Na2S2O3 and water and extracted with CH2Cl2 (2×). The combined organic layers were washed with saturated NaHCO3, dried (MgSO4), filtered and evaporated. Flash chromatography (0-40% ethyl acetate in hexanes) afforded 13.12 g (96%) of methyl 3-{[2-(5-bromo-1,3-thiazol-2-yl)propan-2-yl]sulfonyl}propanoate as a white solid. ESI: [M+H]+ m/z 355.9/357.9.

Workup

  1. additionwas added
  2. extractionextracted with CH2Cl2 (2×)
  3. washThe combined organic layers were washed with saturated NaHCO3
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c7d37a4e5e6e448ba6d62a6474a12201
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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