m-Chloroperbenzoic acid → (7S)-3-((S)-1-(4-bromophenyl)ethyl)-7-((2-methyloxiran-2-yl)methyl)-7-phenyl-1,3-oxazepan-2-one

HRID 219628Notes

Reaction equation

HRID 219628 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:16][CH2:15][CH2:14][C@:13]([CH2:23][C:24]([CH3:26])=[CH2:25])([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:12][C:11]2=[O:27])[CH3:9])=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:36])C=1>C(Cl)Cl.C(OC)(C)(C)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:16][CH2:15][CH2:14][C@:13]([CH2:23][C:24]3([CH3:26])[CH2:25][O:36]3)([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[O:12][C:11]2=[O:27])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59190390(S)-3-((S)-1-(4-bromophenyl)ethyl)-7-(2-methylallyl)-7-phenyl-1,3-oxazepan-2-one

Product 1

HCID 59190382(7S)-3-((S)-1-(4-bromophenyl)ethyl)-7-((2-methyloxiran-2-yl)methyl)-7-phenyl-1,3-oxazepan-2-oneYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of (S)-3-((S)-1-(4-bromophenyl)ethyl)-7-(2-methylallyl)-7-phenyl-1,3-oxazepan-2-one (300 mg, 0.7 mmol) in dry CH2Cl2 (20 mL) was added m-CPBA (605 mg, 3.5 mmol) at room temperature. The reaction mixture was stirred until the starting material was completed. The mixture was diluted with (CH3)3COCH3 (30 mL), washed by 30% Na2S2O3, and NaHCO3 (aq.) for three times, dried over Na2SO4, filtered, and concentrated to give (7S)-3-((S)-1-(4-bromophenyl)ethyl)-7-((2-methyloxiran-2-yl)methyl)-7-phenyl-1,3-oxazepan-2-one (280 mg, 90%), which was used directly for the next step without further purification.

Workup

  1. washwashed by 30% Na2S2O3, and NaHCO3 (aq.) for three times
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0b926507e3d64719bc0befe9f66c58d2
Source dataset
uspto-grants-2012_06
Patent number
US08202857B2

Reaction notes

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