m-Chloroperbenzoic acid → [4-(4-Oxiranylmethoxyphenyl)butyl]carbamic acid benzyl ester

HRID 1795037Notes

Reaction equation

HRID 1795037 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([O:19][C:20](=[O:36])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH:34]=[CH2:35])=[CH:28][CH:27]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[CH2:12]([O:19][C:20](=[O:36])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH:34]2[CH2:35][O:6]2)=[CH:28][CH:27]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11551825[4-(4-Allyloxyphenyl)butyl]carbamic acid benzyl ester

Product 1

HCID 85988461[4-(4-Oxiranylmethoxyphenyl)butyl]carbamic acid benzyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloro-peroxybenzoic acid (2.46 g, 14.25 mmol) was added into a methylene chloride solution (100 mL) of 38 (1.86 g, 5.48 mmol), and the reaction was stirred at room temperature overnight. After that, the solvent was removed under reduced pressure and the residue was purified by flash chromatography (silica gel, 8:1:1 methylene chloride/hexane/ethyl acetate). To eliminate the admixture of benzoic acid the methylene chloride solution of the product was sequentially washed with a saturated aqueous solution of sodium hydrogen carbonate and water, then dried over anhydrous sodium sulfate and evaporated to provide 1.4 g (72%) of 39 as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 1.57 (m, 4H), 2.56 (m, 2H), 2.78 (m, 1H), 2.91 (m, 1H), 3.21 (m, 2H), 3.36 (m, 1H), 3.97 (m, 1H), 4.19 (m, 1H), 5.08 (s, 2H), 6.82 (d, 2H), 7.06 (d, 2H), 7.72 (s, 5H).

Workup

  1. customAfter that, the solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography (silica gel, 8:1:1 methylene chloride/hexane/ethyl acetate)
  3. washwas sequentially washed with a saturated aqueous solution of sodium hydrogen carbonate and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-377d5c531234470da0753766caa88c4a
Source dataset
uspto-grants-2006_04
Patent number
US07026325B2

Reaction notes

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