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

HRID 254348Notes

Reaction equation

HRID 254348 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, 21), 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, 21), 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-51ec0997d3e748ebbdc48c7bf17d0109
Source dataset
uspto-grants-2011_01
Patent number
US07875619B2

Reaction notes

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