m-Chloroperbenzoic acid → HCID 178472329, compound

HRID 928115Notes

Reaction equation

HRID 928115 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([C@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH2:8])=[N:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:28])C=1>ClCCl>[Br:1][C:2]1[S:6][C:5]([C:7]2([C@H:9]3[CH2:14][CH2:13][C@H:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]3)[CH2:8][O:28]2)=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178437588HCID 178437588, compound

Product 1

HCID 178472329HCID 178472329, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)ethenyl]cyclohexanecarboxylate (308 mg, 0.895 mmol) from Step 1 in dichloromethane (10 mL) was treated portionwise at 0° C. with meta-chloroperbenzoic acid (261 mg, 1.163 mmol, 77%). The mixture was stirred at room temperature for 16 h, diluted with dichloromethane and washed with 2N sodium hydroxide. The aqueous phase was extracted with dichloromethane and the combined organic layers were washed with brine, dried over magnesium sulfate and filtered. The volatiles were removed under reduced pressure and the crude product was purified by chromatography on silica gel (0% to 20% EtOAc in hexanes) to afford ethyl trans-4-[2-(5-bromo-1,3-thiazol-2-yl)oxiran-2-yl]cyclohexanecarboxylate as a colorless oil. MS ESI calc'd. for C14H18BrNO3S [M+H]+ 360, 362. found 360, 362.

Workup

  1. washwashed with 2N sodium hydroxide
  2. extractionThe aqueous phase was extracted with dichloromethane
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe volatiles were removed under reduced pressure
  7. customthe crude product was purified by chromatography on silica gel (0% to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-17b681856cbe44c2840737a9fc72f4d5
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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