m-Chloroperbenzoic acid → 1-[4'-(3-Methyl-4-oxiranylmethyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

HRID 1512617Notes

Reaction equation

HRID 1512617 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([O:14][C:15]([C:17]1([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]4[O:36][N:35]=[C:34]([CH3:37])[C:33]=4[CH2:38][CH:39]=[CH2:40])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[CH2:19][CH2:18]1)=[O:16])[CH3:13]>OP([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>[CH2:12]([O:14][C:15]([C:17]1([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]4[O:36][N:35]=[C:34]([CH3:37])[C:33]=4[CH2:38][CH:39]4[CH2:40][O:9]4)=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[CH2:19][CH2:18]1)=[O:16])[CH3:13]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 665772401-[4'-(4-Allyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 866524011-[4'-(3-Methyl-4-oxiranylmethyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24203Sodium Phosphate, DibasicSolvent2×

Procedure

m-Chloroperbenzoic acid (77%, 0.565 g, 2.52 mmol) was washed 4× with a solution of sodium phosphate dibasic (0.1 M aq., 7 mL) then dissolved in CH2Cl2 (4 mL). The solution was added to 1-[4′-(4-Allyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.244 g, 0.63 mmol) in CH2Cl2 (3 mL) followed by sodium phosphate dibasic (0.1 M aq., 7 mL). After 3.5 hours an additional portion of m-chloroperbenzoic acid (0.55 g) was rinsed 4× with sodium phosphate dibasic (0.1 M aq., 7 mL) and added to the reaction and stirring continued overnight. The reaction was then submitted to standard aqueous workup and purified via silica gel chromatography (0-30% EtOAc in hexanes) to give the title compound.

Workup

  1. washAfter 3.5 hours an additional portion of m-chloroperbenzoic acid (0.55 g) was rinsed 4× with sodium phosphate dibasic (0.1 M aq., 7 mL)
  2. additionadded to the reaction
  3. custompurified via silica gel chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f00a7aa1ef19423fbb73c34ac422ae9b
Source dataset
uspto-grants-2012_07
Patent number
US08217066B2

Reaction notes

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